Asymmetric Synthesis of New Chiral β-amino Acid Derivatives by Mannich-type Reactions of Chiral N- Sulfinyl Imidates with N-Tosyl Aldimines
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- Παρθενορή Αλεξόπουλος
- 5 χρόνια πριν
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1 Asymmetric Synthesis of New Chiral β-amino Acid Derivatives by Mannich-type Reactions of Chiral N- Sulfinyl Imidates with N-yl Aldimines Filip Colpaert, Sven Mangelinckx, and Norbert De Kimpe Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium Supporting Information Table of Contents I. General methods... S-2 II. Synthetic procedures and spectral data... S-3 1. Synthesis of β-(sulfonylamino)sulfinylimidates 3... S-3 2. N-Deprotection of β-(sulfonylamino)sulfinylimidates 3 to the corresponding β- sulfonylamino imidate hydrochlorides 4... S-8 3. Synthesis of chiral β-sulfonylamino amides 5... S Synthesis of chiral β-sulfonylamino esters 6... S Synthesis of chiral γ-sulfonylamino alcohols 7... S Synthesis of chiral N-tosylazetidines 8... S-20 III. Copies of 1 H NMR and 13 C NMR spectra of 3, 4, 5, 6, 7 and 8... S-22 S-1
2 I. General methods Tetrahydrofuran (THF) and diethyl ether (Et 2 O) were freshly distilled under a nitrogen atmosphere from sodium/benzophenone ketyl. All other chemicals were of commercial grade and used without further purification. Petroleum ether refers to the C boiling fraction. 1 H NMR (300 MHz), 13 C NMR (75 MHz) spectra were recorded in deuterated solvents with tetramethylsilane (TMS, δ = 0 ppm) as internal standard unless specified otherwise. Mass spectra were recorded using a direct inlet system (ESI, 4000 V). IR spectra were obtained from samples in neat form with an ATR (Attenuated Total Reflectance) accessory. Elementary analyses were performed using a Perkin-Elmer 2400 (Series II, CHNS/O) elementary analyzer. The purification of the reaction mixtures was performed by column chromatography with silica gel (particle size mm, pore diameter ca. 6 nm). S-2
3 II. Synthetic procedures and spectral data 1. Synthesis of β-(sulfonylamino)sulfinylimidates 3 Table S1. Optimization of the addition reaction of N-sulfinyl imidate 1 across aldimines 2 R N tbu S O 1 1) base 2) 1.0 equiv N X H 2a X = Cl X 2b X = H 2c X = R S (R S,S,R)-anti-3a-c tbu tbu N S O N S O + R S + R R R X (R S,R,S)-anti-3a-c X S S N tbu S O (R S,S,S)-syn-3a-c entry X 1 (equiv) reaction conditions (R S,S,R)-3/(R S,R,S)-3/ (R S,S,S)-3 a anti/syn a yield (%) 1 Cl 1.5 1) 5 mol% DBU, DMF, 0 C ) 0 C to rt, 72 h 2 Cl 1.0 1) 1.05 equiv LDA, THF, -78 C, 2 min ) -78 C to 0 C, 3 h 3 Cl 2.0 1) 2.0 equiv LiHMDS, THF, -78 C, 45 min 67/26/7 93/7-2) -78 C, 1 h 4 Cl 2.0 1) 2.0 equiv LiHMDS, THF, -78 C, 45 min 57/37/6 94/6-2) -78 C to rt, 1 h 5 Cl 2.0 1) 2.0 equiv KHMDS, THF, -78 C, 45 min 62/16/22 78/22-2) -78 C, 1 h 6 Cl 2.0 1) 2.0 equiv LiHMDS, THF, -78 C, 45 min 45/49/6 94/ equiv ZnCl 2, -78 C, 15 min 2) -78 C, 1 h 7 Cl 1.2 1) 1.2 equiv LiHMDS, THF, -78 C, 45 min 2) -78 C, 1 h 75/25/0 > 99/1 (R S,S,R)-3a (59), (R S,R,S)-3a (21) 8 H 1.2 1) 1.2 equiv LiHMDS, THF, -78 C, 45 min 2) -78 C, 1 h 67/26/7 93/7 (R S,S,R)-3b (58), (R S,R,S)-3b (24), (R S,S,S)-3b (5) ) 1.2 equiv LiHMDS, THF, -78 C, 45 min 2) -78 C, 1 h 38/60/2 98/2 (R S,S,R)-3c (34), (R S,R,S)-3c (50) 10 Cl 1.2 1) 1.2 equiv KHMDS, THF, -78 C, 45 min 63/12/25 75/25-2) -78 C, 1 h 11 Cl 1.2 1) 1.2 equiv NaHMDS, THF, -78 C, 45 min 51/22/27 73/27-2) -78 C, 1 h 12 Cl 1.2 1) 1.2 equiv LiHMDS, Toluene, -78 C, 45 min 67/26/7 93/7-2) -78 C, 1 h 13 Cl 1.2 1) 1.2 equiv LiHMDS, THF, -97 C, 45 min 75/18/7 93/7-2) -97 C, 1 h 14 Cl 1.2 1) 1.2 equiv LiHMDS, THF, -78 C, 45 min equiv HMPA, -78 C, 15 min 2) -78 C, 1 h 15 Cl 1.2 1) 1.2 equiv LiHMDS, THF, -78 C, 45 min 87/4/9 91/ equiv MgBr 2, -78 C, 15 min 2) -78 C, 1 h 16 Cl 1.2 1) 1.2 equiv LiHMDS, THF, -97 C, 45 min equiv MgBr 2, -97 C, 15 min 91/0/9 91/9 (R S,S,R)-3a (76), (R S,S,S)-3a (6) 2) -97 C, 1 h 17 Cl 1.2 1) 1.2 equiv KHMDS, THF, -97 C, 45 min 89/1/10 90/ equiv MgBr 2, -97 C, 15 min 2) -97 C, 1 h 18 H 1.2 1) 1.2 equiv LiHMDS, THF, -97 C, 45 min equiv MgBr 2, -97 C, 15 min 2) -97 C, 1 h 89/6/5 95/5 (R S,S,R)-3b (77), (R S,R,S)-3b (3), (R S,S,S)-3b (4) ) 1.2 equiv LiHMDS, THF, -97 C, 45 min 67/30/3 b 97/ equiv MgBr 2, -97 C, 15 min 2) -97 C, 1 h ) 1.2 equiv LiHMDS, THF, -78 C, 45 min equiv MgBr 2, -78 C, 15 min 2) -78 C, 1 h 93/1/6 94/6 (R S,S,R)-3c (73), (R S,S,S)-3c (5) a Determined via 1 H NMR analysis of the crude reaction mixture. b Only 31% conversion of N-sulfinyl imidate 1 into β- (sulfonylamino)sulfinylimidates 3c. S-3
4 The synthesis of β-(sulfonylamino)sulfinylimidates 3a is representative. A solution of R s - methyl N-tert-butanesulfinyl propanimidate (1.0 equiv, 2.73 g, mmol) in THF (30 ml) was cooled to -97 C. A 1.0 M solution of LiHMDS (1.0 equiv, ml, mmol) in THF was slowly added and the resulting solution was stirred for 45 minutes at -97 C. After deprotonation a solution of MgBr 2 (1.0 equiv, 2.63 g, mmol) in THF (25mL) was added dropwise and the reaction mixture was stirred for 15 minutes at -97 C. A solution of N-(4- chloro-benzylidene)-4-methylbenzenesulfonamide (0.83 equiv, 3.50 g, mmol) in THF (15 ml) was then added dropwise and the reaction mixture was stirred at -97 C for 1.0 hours. To the reaction mixture was added a saturated solution of 4 Cl (5 ml), followed by a 1.0 N aqueous solution of NaOH (20 ml). The aqueous phase was extracted with Et 2 O (3 x 20 ml). The combined organic phases were dried (MgSO 4 ), filtered and evaporated in vacuo. The crude product was purified by flash chromatography to yield 4.40 g (9.06 mmol) of pure (R S,S,R)-methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)-N-tertbutanesulfinyl propanimidate (R S,S,R)-anti-3a and 0.35 g (0.72 mmol) of pure (R S,S,S)-methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)-N-tert-butanesulfinyl propanimidate (R S,S,S)-syn-3a. (R S,S,R)-Methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)-N-tertbutanesulfinyl propanimidate (R S,S,R)-anti-3a. R f = 0.14 (petroleum ether/ Et 2 O 3:7). White crystals, yield 76%. [α] D (c 0.4, CHCl 3 ). Mp C. IR (cm -1 ): ν max 750, 1035, 1160, 1611, H NMR (300 MHz, CDCl 3 ): δ 0.94 (3H, d, J = 7.2 Hz), 1.23 (9H, s), 2.31 (3H, s), 3.74 (3H, s), (1H, m), 4.46 (1H, d x d, J = 9.6, 9.6 Hz), 6.39 (1H, d, J = 9.6 Hz), (6H, m), 7.41 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 16.0, 21.5, 22.2, 43.2, 54.5, 56.8, 60.3, (2C), (2C), (2C), (2C), 133.4, S-4
5 137.1, 137.8, 143.0, MS (ES, pos. mode) m/z (%): 485/487 (M + H +, 100). Anal. Calcd for C 22 H 29 ClN 2 O 4 S 2 : C 54.47; H 6.03; N Found: C 54.57; H 5.95; N (R S,R,S)-Methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)-N-tertbutanesulfinyl propanimidate (R S,R,S)-anti-3a. R f = 0.33 (petroleum ether/ Et 2 O 6:4). Colourless oil, yield 21%. [α] D (c 0.8, CHCl 3 ). IR (cm -1 ): ν max 751, 1160, 1286, H NMR (300 MHz, CDCl 3 ): δ 0.84 (3H, d, J = 7.2 Hz), 1.26 (9H, s), 2.23 (3H, s), (1H, m), 3.66 (3H, s), 4.19 (1H, d x d, J = 10.7, 8.3 Hz), 6.89 (2H, d, J = 8.3 Hz), 6.94 (4H, s), 7.22 (2H, d, J = 4.4 Hz), 7.32 (1H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 14.7, 21.4, 22.0, 44.5, 54.9, 57.3, 59.8, (2C), (2C), (4C), 133.5, 137.7, 138.6, 142.3, MS (ES, pos. mode) m/z (%): 485/487 (M + H +, 100). Anal. Calcd for C 22 H 29 ClN 2 O 4 S 2 : C 54.47; H 6.03; N Found: C 54.78; H 5.98; N (R S,S,S)-Methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)-N-tertbutanesulfinyl propanimidate (R S,S,S)-syn-3a. R f = 0.08 (petroleum ether/ Et 2 O 3:7). White crystals, yield 6%. [α] D (c 0.2, CHCl 3 ). Mp C. IR (cm -1 ): ν max 1049, 1160, 1286, H NMR (300 MHz, CDCl 3 ): δ 1.04 (9H, s), 1.37 (3H, d, J = 6.6 Hz), 2.33 (3H, s), 3.51 (3H, s), (1H, m), 4.43 (1H, d x d, J = 9.6, 9.6 Hz), 6.39 (1H, d, J = 9.6 Hz), (6H, m), 7.42 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 16.0, 21.5, 21.9, 43.9, 54.0, 56.2, 60.0, (2C), (2C), (2C), (2C), 133.4, 138.0, 138.1, 143.0, MS (ES, pos. mode) m/z (%): 485/487 (M + H +, 100). Anal. Calcd for C 22 H 29 ClN 2 O 4 S 2 : C 54.47; H 6.03; N Found: C 54.71; H 5.92; N (R S,S,R)-Methyl 2-methyl-3-phenyl-3-(p-toluenesulfonylamino)-N-tert-butanesulfinyl propanimidate (R S,S,R)-anti-3b. R f = 0.18 (petroleum ether/ Et 2 O 3:7). White crystals, yield S-5
6 77%. [α] D (c 0.4, CHCl 3 ). Mp C. IR (cm -1 ): ν max 1038, 1161, 1614, 2951, H NMR (300 MHz, CDCl 3 ): δ 0.97 (3H, d, J = 7.2 Hz), 1.18 (9H, s), 2.30 (3H, s), 3.73 (3H, s), (1H, m), 4.43 (1H, d x d, J = 9.6, 9.6 Hz), 5.56 (1H, d, J = 9.6 Hz), (7H, m), 7.45 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 15.6, 21.4, 22.0, 43.0, 54.3, 56.3, 60.7, (2C), (2C), 127.6, (2 C), (2C), 137.6, 138.6, 142.8, MS (ES, pos. mode) m/z (%): 451 (M + H +, 100). Anal. Calcd for C 22 H 30 N 2 O 4 S 2 : C 58.64; H 6.71; N Found: C 58.31; H 6.33; N (R S,R,S)-Methyl 2-methyl-3-phenyl-3-(p-toluenesulfonylamino)-N-tert-butanesulfinyl propanimidate (R S,R,S)-anti-3b. R f = 0.49 (petroleum ether/ Et 2 O 3:7). White crystals, yield 24%. [α] D (c 0.9, CHCl 3 ). Mp C. IR (cm -1 ): ν max 1032, 1159, 1613, 2925, H NMR (300 MHz, CDCl 3 ): δ 0.92 (3H, d, J = 6.6 Hz), 1.36 (9H, s), 2.26 (3H, s), (1H, m), 3.75 (3H, s), 4.30 (1H, d x d, J = 10.5, 8.8 Hz), 6.91 (2H, d, J = 8.3 Hz), (5H, m), 7.31 (3H, d, J = 8.8 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 14.7, 21.3, 22.0, 44.6, 54.7, 57.1, 60.3, (3C), 127.4, (3C), 128.2, 128.7, 138.6, 139.2, 141.8, MS (ES, pos. mode) m/z (%): 451 (M + H +, 100). Anal. Calcd for C 22 H 30 N 2 O 4 S 2 : C 58.64; H 6.71; N Found: C 58.37; H 6.45; N (R S,S,S)-Methyl 2-methyl-3-phenyl-3-(p-toluenesulfonylamino)-N-tert-butanesulfinyl propanimidate (R S,S,S)-syn-3b. R f = 0.10 (petroleum ether/ Et 2 O 3:7). White crystals, yield 5%. [α] D (c 0.3, CHCl 3 ). Mp C. IR (cm -1 ): ν max 1057, 1160, 1291, 1601, H NMR (300 MHz, CDCl 3 ): δ 1.00 (9H, s), 1.37 (3H, d, J = 7.2 Hz), 2.31 (3H, s), 3.50 (3H, s), (1H, m), 4.47 (1H, d x d, J = 9.6, 9.6 Hz), 5.62 (1H, d, J = 9.6 Hz), (7H, m), 7.45 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 15.6, 21.5, 21.8, 44.0, 54.0, 56.0, 60.5, (2C), (2C), 127.7, (2C), (2C), 137.8, 139.3, 142.8, S-6
7 MS (ES, pos. mode) m/z (%): 451 (M + H +, 100). Anal. Calcd for C 22 H 30 N 2 O 4 S 2 : C 58.64; H 6.71; N Found: C 58.44; H 6.44; N (R S,S,R)-Methyl 2-methyl-3-(4-methoxyphenyl)-3-(p-toluenesulfonylamino)-N-tertbutanesulfinyl propanimidate (R S,S,R)-anti-3c. R f = 0.13 (petroleum ether/ Et 2 O 3:7). White crystals, yield 73%. [α] D (c 0.5, CHCl 3 ). Mp C. IR (cm -1 ): ν max 1159, 1610, H NMR (300 MHz, CDCl 3 ): δ 0.95 (3H, d, J = 6.6 Hz), 1.20 (9H, s), 2.31 (3H, s), 3.72 (3H, s), 3.73 (3H, s), (1H, m), 4.38 (1H, d x d, J = 9.6, 9.6 Hz), 5.53 (1H, d, J = 9.6 Hz), 6.60 (2H, d, J = 8.3 Hz), 6.87 (2H, d, J = 8.3 Hz), 7.04 (2H, d, J = 8.3 Hz), 7.44 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 15.7, 21.5, 22.2, 43.2, 54.4, 55.3, 56.5, 60.4, (2C), (2C), (2C), (2C), 130.9, 137.9, 142.8, 159.1, MS (ES, pos. mode) m/z (%): 481 (M + H +, 100). Anal. Calcd for C 23 H 32 N 2 O 5 S 2 : C 57.47; H 6.71; N Found: C 57.50; H 6.38; N (R S,R,S)-Methyl 2-methyl-3-(4-methoxyphenyl)-3-(p-toluenesulfonylamino)-N-tertbutanesulfinyl propanimidate (R S,R,S)-anti-3c. R f = 0.42 (petroleum ether/ Et 2 O 3:7). White crystals, yield 50%. [α] D (c 0.5, CHCl 3 ). Mp C. IR (cm -1 ): ν max 1028, 1160, 1296, 1593, 2953, H NMR (300 MHz, CDCl 3 ): δ 0.92 (3H, d, J = 6.6 Hz), 1.33 (9H, s), 2.27 (3H, s), (1H, m), 3.72 (3H, s), 3.75 (3H, s), 4.26 (1H, d x d, J = 10.7, 8.8 Hz), 6.59 (2H, d, J = 8.3 Hz), 6.94 (2H, d, J = 8.3 Hz), 7.00 (2H, d, J = 8.3 Hz), 7.25 (1H, d, J = 8.8 Hz), 7.31 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 14.8, 21.4, 22.1, 44.8, 54.8, 55.3, 57.2, 60.0, (2C), (2C), (2C), (2C), 131.3, 138.9, 141.8, 159.1, MS (ES, pos. mode) m/z (%): 481 (M + H +, 100). Anal. Calcd for C 23 H 32 N 2 O 5 S 2 : C 57.47; H 6.71; N Found: C 57.09; H 6.44; N S-7
8 (R S,S,S)-Methyl 2-methyl-3-(4-methoxyphenyl)-3-(p-toluenesulfonylamino)-N-tertbutanesulfinyl propanimidate (R S,S,S)-syn-3c. R f = 0.07 (petroleum ether/ Et 2 O 3:7). White crystals, yield 5%. [α] D (c 0.2, CHCl 3 ). Mp C. IR (cm -1 ): ν max 1047, 1159, 1249, 1605, H NMR (300 MHz, CDCl 3 ): δ 1.02 (9H, s), 1.36 (3H, d, J = 6.6 Hz), 2.32 (3H, s), 3.50 (3H, s), (1H, m), 4.41 (1H, d x d, J = 9.3, 9.3 Hz), 5.79 (1H, d, J = 9.3 Hz), (2H, m), (4H, m), 7.45 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 15.8, 21.5, 21.9, 44.1, 53.9, 55.3, 56.0, 60.0, (2C), (2C), (2C), (2C), 131.6, 138.0, 142.7, 159.0, MS (ES, pos. mode) m/z (%): 481 (M + H +, 100). Anal. Calcd for C 23 H 32 N 2 O 5 S 2 : C 57.47; H 6.71; N Found: C 57.29; H 6.49; N N-Deprotection of β-(sulfonylamino)sulfinylimidates 3 to the corresponding β- sulfonylamino imidate hydrochlorides 4 The synthesis of (S,R)-methyl 2-methyl-3-(4-chlorophenyl)-3-(ptoluenesulfonylamino)propanimidate hydrochloride (S,R)-anti-4a is representative. To a solution of (R S,S,R)-methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)-N-tertbutanesulfinyl propanimidate (R S,S,R)-anti-3a (2.31 g, 4.77 mmol) in ethanol (40 ml) was added dropwise a 4.0 M solution of dioxane.hcl (2.0 equiv, 2.38 ml, 9.53 mmol) at 0 C. The mixture was allowed to stir for 0.5 hour at 0 C. Then the reaction mixture was concentrated in vacuo. Precipitation in diethyl ether afforded 1.69 g (4.05 mmol) of pure (S,R)-methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)propanimidate hydrochloride (S,R)-anti-4a. (S,R)-Methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)propanimidate hydrochloride (S,R)-anti-4a. White crystals, yield 85%. [α] D (c 0.5, DMF). Mp C. IR (cm -1 ): ν max 1090, 1159, 1655, 2873, H NMR (300 MHz, CDCl 3 ): δ S-8
9 0.99 (3H, d, J = 7.2 Hz), 2.31 (3H, s), (1H, m), 4.36 (1H, d x d, J = 10.5, 10.5 Hz), 4.46 (3H, s), 6.98 (2H, d, J = 8.3 Hz), 7.05 (2H, d, J = 8.3 Hz), 7.13 (2H, d, J = 8.3 Hz), 7.37 (2H, d, J = 8.3 Hz), 8.20 (1H, d, J = 10.5 Hz), (1H, br s), (1H, br s). 13 C NMR (75 MHz, CDCl 3 ): δ 14.1, 21.5, 44.7, 60.6, 61.4, (2C), (2C), (2C), (2C), 134.2, 135.3, 137.5, 143.1, MS (ES, pos. mode) m/z (%): 381/383 (M + H + - HCl, 100). Anal. Calcd for C 18 H 22 Cl 2 N 2 O 3 S: C 51.80; H 5.31; N Found: C 51.54; H 4.93; N (R,S)-Methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)propanimidate hydrochloride (R,S)-anti-4a. White crystals, yield 69%. [α] D (c 0.4, DMF). Mp C. IR (cm -1 ): ν max 1089, 1158, 1657, 2878, H NMR (300 MHz, CDCl 3 ): δ 0.99 (3H, d, J = 6.1 Hz), 2.31 (3H, s), (1H, m), 4.36 (1H, d x d, J = 10.5, 10.5 Hz), 4.46 (3H, s), 6.97 (2H, d, J = 8.3 Hz), 7.04 (2H, d, J = 8.3 Hz), 7.12 (2H, d, J = 8.3 Hz), 7.37 (2H, d, J = 8.3 Hz), 8.21 (1H, d, J = 10.5 Hz), (2H, br s). 13 C NMR (75 MHz, CDCl 3 ): δ 14.1, 21.5, 44.7, 60.6, 61.5, (2C), (2C), (2C), (2C), 134.2, 135.3, 137.5, 143.1, MS (ES, pos. mode) m/z (%): 381/383 (M + H + - HCl, 100). Anal. Calcd for C 18 H 22 Cl 2 N 2 O 3 S: C 51.80; H 5.31; N Found: C 51.63; H 5.13; N (S,R)-Methyl 2-methyl-3-phenyl-3-(p-toluenesulfonylamino)propanimidate hydrochloride (S,R)-anti-4b. White crystals, yield 87%. [α] D (c 0.4, DMF). Mp C. IR (cm -1 ): ν max 1090, 1160, 1330, 1654, 2876, H NMR (300 MHz, CDCl 3 ): δ 0.97 (3H, d, J = 6.6 Hz), 2.27 (3H, s), (1H, m), 4.36 (1H, d x d, J = 10.5, 10.5 Hz), 4.45 (3H, s), 6.95 (2H, d, J = 8.3 Hz), (5H, m), 7.38 (2H, d, J = 8.3 Hz), 7.95 (1H, d, J = 10.5 Hz), (1H, br s), (1H, br s). 13 C NMR (75 MHz, CDCl 3 ): δ 14.0, 21.4, 44.9, 61.2, 61.3, (2C), (2C), 128.1, (2C), (2C), 136.9, S-9
10 137.7, 142.7, MS (ES, pos. mode) m/z (%): 347 (M + H + - HCl, 100). Anal. Calcd for C 18 H 23 Cl 2 N 2 O 3 S: C 56.46; H 6.05; N Found: C 56.11; H 6.31; N (R,S)-Methyl 2-methyl-3-phenyl-3-(p-toluenesulfonylamino)propanimidate hydrochloride (R,S)-anti-4b. White crystals, yield 83%. [α] D (c 0.3, DMF). Mp C. IR (cm -1 ): ν max 1090, 1160, 1330, 1650, 2880, H NMR (300 MHz, CDCl 3 ): δ 0.97 (3H, d, J = 6.6 Hz), 2.26 (3H, s), (1H, m), 4.37 (1H, d x d, J = 10.5, 10.5 Hz), 4.44 (3H, s), 6.94 (2H, d, J = 8.3 Hz), (5H, m), 7.38 (2H, d, J = 8.3 Hz), 7.98 (1H, d, J = 10.5 Hz), (2H, br s). 13 C NMR (75 MHz, CDCl 3 ): δ 14.0, 21.4, 44.9, 61.2, 61.5, (2C), (2C), 128.1, (2C), (2C), 137.0, 137.7, 142.7, MS (ES, pos. mode) m/z (%): 347 (M + H + - HCl, 100). Anal. Calcd for C 18 H 23 Cl 2 N 2 O 3 S: C 56.46; H 6.05; N Found: C 56.80; H 6.09; N (S,S)-Methyl 2-methyl-3-phenyl-3-(p-toluenesulfonylamino)propanimidate hydrochloride (S,S)-syn-4b. White crystals, yield 63%. [α] D (c 0.2, DMF). Mp decomposition at C. IR (cm -1 ): ν max 1158, 1667, 2872, H NMR (300 MHz, CDCl 3 ): δ 1.33 (3H, d, J = 6.6 Hz), 2.27 (3H, s), (1H, m), 4.18 (3H, s), 4.68 (1H, d x d, J = 9.4, 7.7 Hz), 6.99 (2H, d, J = 8.3 Hz), (5H, m), 7.50 (2H, d, J = 8.3 Hz), 7.64 (1H, d, J = 9.4 Hz), (1H, br s), (1H, br s). 13 C NMR (75 MHz, CDCl 3 ): δ 13.7, 21.4, 44.9, 60.4, 60.5, (2C), (2C), 127.9, (2C), (2C), 136.2, 137.4, 142.9, MS (ES, pos. mode) m/z (%): 347 (M + H + - HCl, 100). Anal. Calcd for C 18 H 23 Cl 2 N 2 O 3 S: C 56.46; H 6.05; N Found: C 56.76; H 5.98; N (S,R)-Methyl 2-methyl-3-(4-methoxyphenyl)-3-(p-toluenesulfonylamino)propanimidate hydrochloride (S,R)-anti-4c. White crystals, yield 80%. [α] D (c 0.2, DMF). Mp C. IR (cm -1 ): ν max 1152, 1322, 1640, 2936, H NMR (300 MHz, CDCl 3 ): δ S-10
11 0.97 (3H, d, J = 5.0 Hz), 2.28 (3H, s), (1H, m), 3.73 (3H, s), 4.32 (1H, d x d, J = 9.9, 9.9 Hz), 4.43 (3H, s), 6.63 (2H, d, J = 8.3 Hz), 6.97 (2H, d, J = 8.3 Hz), 7.10 (2H, d, J = 8.3 Hz), 7.40 (2H, d, J = 8.3 Hz), 8.03 (1H, d, J = 9.9 Hz), (2H, br s). 13 C NMR (75 MHz, CDCl 3 ): δ 14.1, 21.4, 45.0, 55.2, 60.7, 61.0, (2C), (2C), (2C), 128.9, (2C), 137.7, 142.5, 159.3, MS (ES, pos. mode) m/z (%): 377 (M + H + - HCl, 100). Anal. Calcd for C 19 H 25 ClN 2 O 4 S: C 55.26; H 6.10; N Found: C 55.12; H 6.00; N (R,S)-Methyl 2-methyl-3-(4-methoxyphenyl)-3-(p-toluenesulfonylamino)-propanimidate hydrochloride (R,S)-anti-4c. White crystals, yield 92%. [α] D (c 0.2, DMF). Mp C. IR (cm -1 ): ν max 1157, 1321, 1640, 2936, H NMR (300 MHz, CDCl 3 ): δ 0.97 (3H, d, J = 5.5 Hz), 2.28 (3H, s), (1H, m), 3.73 (3H, s), 4.30 (1H, d x d, J = 9.9, 9.9 Hz), 4.43 (3H, s), 6.63 (2H, d, J = 8.3 Hz), 6.97 (2H, d, J = 8.3 Hz), 7.10 (2H, d, J = 8.3 Hz), 7.39 (2H, d, J = 8.3 Hz), 7.91 (1H, d, J = 9.9 Hz), (2H, br s). 13 C NMR (75 MHz, CDCl 3 ): δ 14.1, 21.5, 45.1, 55.3, 60.8, 61.4, (2C), (2C), (2C), 129.0, (2C), 137.8, 142.6, 159.4, MS (ES, pos. mode) m/z (%): 377 (M + H + - HCl, 100). Anal. Calcd for C 19 H 25 ClN 2 O 4 S: C 55.26; H 6.10; N Found: C 55.04; H 6.02; N Synthesis of chiral β-sulfonylamino amides 5 The synthesis of (S,R)-methyl 2-methyl-3-(4-chlorophenyl)-3-(ptoluenesulfonylamino)propanamide (S,R)-anti-5a is representative. (S,R)-Methyl 2-methyl-3- (4-chlorophenyl)-3-(p-toluenesulfonylamino)propanimidate hydrochloride (S,R)-anti-4a (0.57 g, 1.37 mmol) was dissolved in chloroform (20 ml). The reaction mixture was stirred for 16 hours at reflux temperature and subsequently evaporated in vacuo. Recrystallization S-11
12 from diethyl ether afforded 0.46 g (1.24 mmol) of pure (S,R)-methyl 2-methyl-3-(4- chlorophenyl)-3-(p-toluenesulfonylamino)propanamide (S,R)-anti-5a. (S,R)-Methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)propanamide (S,R)-anti-5a. White crystals, yield 91%. [α] D (c 0.3, DMF). Mp C. ee > 98%, HPLC Daicel Chiralcel OD-H column: Hexane (80%) / Ethanol (20%), 0.5 ml min -1, 35 C, t R ((R,S)-anti-5a) = min, t R ((S,R)-anti-5a) = min. IR (cm -1 ): ν max 1156, 1338, 1625, 1641, 3214, 3289, H NMR (300 MHz, CDCl 3 ): δ 1.02 (3H, d, J = 6.6 Hz), 2.33 (3H, s), (1H, m), 4.45 (1H, d x d, J = 8.8, 8.8 Hz), 6.14 (1H, br s), 6.36 (1H, br s), (6H, m), 7.20 (1H, d, J = 8.8 Hz), 7.37 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 16.0, 21.5, 46.4, 60.4, (2C), (2C), (2C), (2C), 133.3, 137.2, 137.5, 143.2, MS (ES, pos. mode) m/z (%): 367/369 (M + H +, 100). Anal. Calcd for C 17 H 19 ClN 2 O 3 S: C 55.66; H 5.22; N Found: C 55.61; H 4.86; N (R,S)-Methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)propanamide (R,S)-anti-5a. White crystals, yield 57%. [α] D (c 0.5, DMF). Mp C. ee > 98%, HPLC Daicel Chiralcel OD-H column: Hexane (80%) / Ethanol (20%), 0.5 ml min -1, 35 C, t R ((R,S)-anti-5a) = min, t R ((S,R)-anti-5a) = min. IR (cm -1 ): ν max 1156, 1338, 1641, 3216, 3288, H NMR (300 MHz, CDCl 3 ): δ 1.19 (3H, d, J = 6.6 Hz), 2.34 (3H, s), 2.56 (1H, quintet, J = 6.6 Hz), 4.47 (1H, d x d, J = 8.5, 6.6 Hz), 5.44 (1H, br s), 5.59 (1H, br s), 6.93 (1H, d, J = 8.5 Hz), (2H, m), (4H, m), 7.45 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 16.3, 21.5, 46.3, 60.2, (2C), (2C), (2C), (2C), 133.3, 137.7, 137.8, 143.1, MS (ES, pos. mode) m/z (%): 367/369 (M + H +, 100). Anal. Calcd for C 17 H 19 ClN 2 O 3 S: C 55.66; H 5.22; N Found: C 55.37; H 5.12; N S-12
13 (S,R)-Methyl 2-methyl-3-phenyl-3-(p-toluenesulfonylamino)propanamide (S,R)-anti-5b. White crystals, yield 77%. [α] D (c 0.3, DMF). Mp C. ee > 98%, HPLC Daicel Chiralcel OD-H column: Hexane (80%) / Ethanol (20%), 0.5 ml min -1, 35 C, t R ((R,S)-anti-5b) = min, t R ((S,R)-anti-5b) = min. IR (cm -1 ): ν max 1156, 1656, 3288, 3371, H NMR (300 MHz, CDCl 3 ): δ 1.12 (3H, d, J = 6.6 Hz), 2.29 (3H, s), 2.60 (1H, quintet, J = 6.6 Hz), 4.48 (1H, d x d, J = 8.8, 6.6 Hz), 5.60 (1H, br s), 5.87 (1H, br s), 6.94 (1H, d, J = 8.8 Hz), (7H, m), 7.44 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 16.2, 21.5, 46.7, 60.8, (2C), (2C), 127.4, (2C), (2C), 137.8, 139.1, 142.8, MS (ES, pos. mode) m/z (%): 333 (M + H +, 100). Anal. Calcd for C 17 H 20 N 2 O 3 S: C 61.42; H 6.06; N Found: C 61.08; H 5.87; N (R,S)-Methyl 2-methyl-3-phenyl-3-(p-toluenesulfonylamino)propanamide (R,S)-anti-5b. White crystals, yield 82%. [α] D (c 0.5, DMF). Mp C. ee > 98%, HPLC Daicel Chiralcel OD-H column: Hexane (80%) / Ethanol (20%), 0.5 ml min -1, 35 C, t R ((R,S)-anti-5b) = min, t R ((S,R)-anti-5b) = min. IR (cm -1 ): ν max 1151, 1656, 3198, H NMR (300 MHz, CDCl 3 ): δ 1.11 (3H, d, J = 7.1 Hz), 2.33 (3H, s), 2.67 (1H, quintet, J = 7.1 Hz), 4.52 (1H, d x d, 9.0, 7.1 Hz), 5.89 (1H, br s), 6.18 (1H, br s), (8H, m), 7.46 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 16.1, 21.5, 46.7, 60.9, (4C), 127.3, (2C), (2C), 137.7, 138.9, 142.7, MS (ES, pos. mode) m/z (%): 333 (M + H +, 100). Anal. Calcd for C 17 H 20 N 2 O 3 S: C 61.42; H 6.06; N Found: C 61.17; H 6.06; N (S,R)-Methyl 2-methyl-3-(4-methoxyphenyl)-3-(p-toluenesulfonylamino)propanamide (S,R)-anti-5c. White crystals, yield 86%. [α] D (c 0.5, DMF). Mp C. ee > 98%, HPLC Daicel Chiralcel OD-H column: Hexane (80%) / Ethanol (20%), 0.5 ml min -1, 35 C, t R ((R,S)-anti-5c) = min, t R ((S,R)-anti-5c) = min. IR (cm -1 ): ν max 1151, S-13
14 1321, 1617, 1639, 3215, 3286, H NMR (300 MHz, DMSO-d 6 ): δ 0.68 (3H, d, J = 6.6 Hz), 2.25 (3H, s), (1H, m), 3.65 (3H, s), 4.34 (1H, d x d, J = 9.4, 9.4 Hz), 6.59 (2H, d, J = 8.3 Hz), 6.93 (2H, d, J = 8.3 Hz), 7.04 (2H, d, J = 8.3 Hz), 7.30 (2H, d, J = 8.3 Hz), 7.96 (1H, d, J = 9.4 Hz). 13 C NMR (75 MHz, DMSO-d 6 ): δ 15.4, 20.7, 45.6, 54.8, 59.5, (2C), (2C), 128.1, (2C), (2C), 138.7, 141.3, 157.9, MS (ES, pos. mode) m/z (%): 361 (M + H +, 100). Anal. Calcd for C 18 H 22 N 2 O 4 S: C 59.65; H 6.12; N Found: C 59.40; H 5.95; N (R,S)-Methyl 2-methyl-3-(4-methoxyphenyl)-3-(p-toluenesulfonylamino)propanamide (R,S)-anti-5c. White crystals, yield 88%. [α] D (c 0.4, DMF). Mp C. ee > 98%, HPLC Daicel Chiralcel OD-H column: Hexane (80%) / Ethanol (20%), 0.5 ml min -1, 35 C, t R ((R,S)-anti-5c) = min, t R ((S,R)-anti-5c) = min. IR (cm -1 ): ν max 1151, 1321, 1617, 1639, 3216, 3286, H NMR (300 MHz, DMSO-d 6 ): δ 0.68 (3H, d, J = 7.1 Hz), 2.25 (3H, s), (1H, m, J = 7.1 Hz), 3.65 (3H, s), 4.34 (1H, d x d, J = 9.4, 9.4 Hz), 6.59 (2H, d, J = 8.3 Hz), 6.93 (2H, d, J = 8.3 Hz), 7.04 (2H, d, J = 8.3 Hz), 7.30 (2H, d, J = 8.3 Hz), 7.97 (1H, d, J = 9.4 Hz). 13 C NMR (75 MHz, DMSO-d 6 ): δ 15.4, 20.7, 45.6, 54.9, 59.5, (2C), (2C), 128.1, (2C), (2C), 138.7, 141.3, 158.0, MS (ES, pos. mode) m/z (%): 361 (M + H +, 100). Anal. Calcd for C 18 H 22 N 2 O 4 S: C 59.65; H 6.12; N Found: C 59.29; H 6.04; N Synthesis of chiral β-sulfonylamino esters 6 The synthesis of (S,R)-methyl 2-methyl-3-(4-chlorophenyl)-3-(ptoluenesulfonylamino)propanoate (S,R)-anti-6a is representative. (S,R)-Methyl 2-methyl-3-(4- chlorophenyl)-3-(p-toluenesulfonylamino)propanimidate hydrochloride (S,R)-anti-4a (0.46 g, 1.11 mmol) was dissolved in H 2 O (15 ml). The reaction mixture was stirred for 7 hours at 55 S-14
15 C and subsequently poured in a saturated aqueous solution of NaHCO 3 (20 ml) and extracted with diethyl ether (3 x 20 ml). The combined organic phases were dried (MgSO 4 ), filtered and evaporated in vacuo. The crude product was purified by flash chromatography to yield 0.32 g of pure (S,R)-methyl 2-methyl-3-(4-chlorophenyl)-3-(ptoluenesulfonylamino)propanoate (S,R)-anti-6a. (S,R)-Methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)propanoate (S,R)- anti-6a. R f = 0.39 (petroleum ether/ Et 2 O 3:7). White crystals, yield 76%. [α] D (c 0.4, CHCl 3 ). Mp C. ee > 98%, HPLC Daicel Chiralcel OD-H column: Hexane (95.5%) / Ethanol (4.5%), 0.5 ml min -1, 35 C, t R ((R,S)-anti-6a) = min, t R ((S,R)-anti- 6a) = min. IR (cm -1 ): ν max 1155, 1734, H NMR (300 MHz, CDCl 3 ): δ 1.16 (3H, d, J = 6.6 Hz), 2.35 (3H, s), 2.79 (1H, quintet, J = 6.6 Hz), 3.56 (3H, s), 4.48 (1H, d x d, J = 8.5, 6.6 Hz), 6.00 (1H, d, J = 8.5 Hz), 6.94 (2H, d, J = 8.3 Hz), 7.09 (4H, d, J = 8.3 Hz), 7.48 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 15.3, 21.5, 46.0, 52.2, 59.8, (2C), (2C), (2C), (2C), 133.4, 137.4, 137.7, 143.2, MS (ES, pos. mode) m/z (%): 380/382 (M + H +, 100). Anal. Calcd for C 18 H 20 ClNO 4 S: C 56.61; H 5.28; N Found: C 56.49; H 5.11; N (R,S)-Methyl 2-methyl-3-(4-chlorophenyl)-3-(p-toluenesulfonylamino)propanoate (R,S)- anti-6a. R f = 0.29 (petroleum ether/ Et 2 O 3:7). White crystals, yield 86%. [α] D (c 0.3, CHCl 3 ). Mp C. ee > 98%, HPLC Daicel Chiralcel OD-H column: Hexane (95.5%) / Ethanol (4.5%), 0.5 ml min -1, 35 C, t R ((R,S)-anti-6a) = min, t R ((S,R)-anti- 6a) = min. IR (cm -1 ): ν max 1156, 1734, H NMR (300 MHz, CDCl 3 ): δ 1.11 (3H, d, J = 7.2 Hz), 2.34 (3H, s), 2.80 (1H, quintet, J = 7.2 Hz), 3.58 (3H, s), 4.48 (1H, d x d, J = 8.5, 7.2 Hz), 6.23 (1H, d, J = 8.5 Hz), 6.95 (2H, d, J = 8.3 Hz), 7.08 (4H, d, J = 8.3 Hz), 7.48 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 15.4, 21.5, 46.0, 52.2, 59.8, (2C), S-15
16 128.2 (2C), (2C), (2C), 133.4, 137.4, 137.7, 143.2, MS (ES, pos. mode) m/z (%): 380/382 (M + H +, 100). Anal. Calcd for C 18 H 20 ClNO 4 S: C 56.61; H 5.28; N Found: C 56.92; H 5.14; N (S,R)-Methyl 2-methyl-3-phenyl-3-(p-toluenesulfonylamino)propanoate (S,R)-anti-6b. R f = 0.38 (petroleum ether/ Et 2 O 3:7). White crystals, yield 72%. [α] D (c 0.3, CHCl 3 ). Mp C. ee > 98%, HPLC Daicel Chiralcel OD-H column: Hexane (95.5%) / Ethanol (4.5%), 0.5 ml min -1, 35 C, t R ((R,S)-anti-6b) = min, t R ((S,R)-anti-6b) = min. IR (cm -1 ): ν max 1163, 1737, 2922, H NMR (300 MHz, CDCl 3 ): δ 1.15 (3H, d, J = 7.2 Hz), 2.32 (3H, s), 2.83 (1H, quintet, J = 7.2 Hz), 3.56 (3H, s), 4.51 (1H, d x d, J = 8.8, 7.2 Hz), 5.93 (1H, d, J = 8.8 Hz), (2H, m), 7.06 (4H, d, J = 8.3 Hz), (3H, m), 7.49 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 15.6, 21.5, 46.1, 52.0, 60.3, (2C), (2C), 127.5, (2C), (2C), 137.9, 139.0, 142.9, MS (ES, pos. mode) m/z (%): 346 (M + H +, 100). Anal. Calcd for C 18 H 21 NO 4 S: C 62.23; H 6.09; N Found: C 62.06; H 6.03; N (R,S)-Methyl 2-methyl-3-phenyl-3-(p-toluenesulfonylamino)propanoate (R,S)-anti-6b. R f = 0.51 (petroleum ether/ Et 2 O 3:7). White crystals, yield 94%. [α] D (c 0.3, CHCl 3 ). Mp C. ee > 98%, HPLC Daicel Chiralcel OD-H column: Hexane (95.5%) / Ethanol (4.5%), 0.5 ml min -1, 35 C, t R ((R,S)-anti-6b) = min, t R ((S,R)-anti-6b) = min. IR (cm -1 ): ν max 1163, 1321, 1737, 2922, H NMR (300 MHz, CDCl 3 ): δ 1.16 (3H, d, J = 7.2 Hz), 2.32 (3H, s), 2.83 (1H, quintet, J = 7.2 Hz), 3.56 (3H, s), 4.50 (1H, d x d, J = 8.8, 6.1 Hz), 5.91 (1H, d, J = 8.8 Hz), (2H, m), 7.06 (4H, d, J = 8.3 Hz), (3H, m), 7.49 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 15.6, 21.5, 46.1, 51.9, 60.3, (2C), (2C), 127.6, (2C), (2C), 137.9, 139.0, 143.0, MS (ES, pos. S-16
17 mode) m/z (%): 346 (M + H +, 100). Anal. Calcd for C 18 H 21 NO 4 S: C 62.23; H 6.09; N Found: C 62.08; H 5.97; N (S,S)-Methyl 2-methyl-3-phenyl-3-(p-toluenesulfonylamino)propanoate (S,S)-syn-6b. R f = 0.42 (petroleum ether/ Et 2 O 3:7). White crystals, yield 63%. [α] D (c 0.3, CHCl 3 ). Mp C. IR (cm -1 ): ν max 1161, 1735, H NMR (300 MHz, CDCl 3 ): δ 1.16 (3H, d, J = 7.2 Hz), 2.32 (3H, s), 2.86 (1H, quintet, J = 7.2 Hz), 3.47 (3H, s), 4.54 (1H, d x d, J = 9.1, 7.2 Hz), 5.87 (1H, d, J = 9.1 Hz), (2H, m), (5H, m), 7.51 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 13.6, 21.5, 46.0, 51.9, 60.0, (2C), (2C), 127.6, (2C), (2C), 137.5, 138.3, 143.1, MS (ES, pos. mode) m/z (%): 346 (M + H +, 100). Anal. Calcd for C 18 H 21 NO 4 S: C 62.23; H 6.09; N Found: C 61.96; H 5.88; N (S,R)-Methyl 2-methyl-3-(4-methoxyphenyl)-3-(p-toluenesulfonylamino)propanoate (S,R)-anti-6c. R f = 0.23 (petroleum ether/ Et 2 O 3:7). White crystals, yield 82%. [α] D (c 0.3, CHCl 3 ). Mp C. ee > 98%, HPLC Daicel Chiralcel OD-H column: Hexane (95.5%) / Ethanol (4.5%), 0.5 ml min -1, 35 C, t R ((R,S)-anti-6c) = min, t R ((S,R)-anti- 6c) = min. IR (cm -1 ): ν max 1159, 1728, 2924, H NMR (300 MHz, CDCl 3 ): δ 1.06 (3H, d, J = 7.2 Hz), 2.30 (3H, s), 2.82 (1H, quintet, J = 7.2 Hz), 3.60 (3H, s), 3.71 (3H, s), 4.47 (1H, d x d, J = 8.8, 7.2 Hz), 6.25 (1H, d, J = 8.8 Hz), 6.62 (2H, d, J = 8.3 Hz), 6.93 (2H, d, J = 8.3 Hz), 7.04 (2H, d, J = 8.3 Hz), 7.48 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 15.1, 21.4, 46.4, 52.0, 55.3, 60.0, (2C), (2C), (2C), (2C), 130.8, 138.0, 142.7, 159.0, MS (ES, neg. mode) m/z (%): 376 (M - H +, 100). Anal. Calcd for C 19 H 23 NO 5 S: C 60.46; H 6.14; N Found: C 60.22; H 6.01; N S-17
18 (R,S)-Methyl 2-methyl-3-(4-methoxyphenyl)-3-(p-toluenesulfonylamino)propanoate (R,S)-anti-6c. R f = 0.24 (petroleum ether/ Et 2 O 3:7). White crystals, yield 78%. [α] D (c 0.3, CHCl 3 ). Mp C. ee > 98%, HPLC Daicel Chiralcel OD-H column: Hexane (95.5%) / Ethanol (4.5%), 0.5 ml min -1, 35 C, t R ((R,S)-anti-6c) = min, t R ((S,R)-anti- 6c) = min. IR (cm -1 ): ν max 1159, 1251, 1728, 2936, H NMR (300 MHz, CDCl 3 ): δ 1.09 (3H, d, J = 7.2 Hz), 2.32 (3H, s), 2.81 (1H, quintet, J = 7.2 Hz), 3.59 (3H, s), 3.73 (3H, s), 4.46 (1H, d x d, J = 8.8, 7.2 Hz), 6.05 (1H, d, J = 8.8 Hz), 6.64 (2H, d, J = 8.3 Hz), 6.92 (2H, d, J = 8.3 Hz), 7.06 (2H, d, J = 8.3 Hz), 7.49 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 15.3, 21.5, 46.3, 52.0, 55.3, 60.0, (2C), (2C), (2C), (2C), 131.0, 138.0, 142.8, 159.0, MS (ES, neg. mode) m/z (%): 376 (M - H +, 100). Anal. Calcd for C 19 H 23 NO 5 S: C 60.46; H 6.14; N Found: C 60.36; H 5.85; N Synthesis of chiral γ-sulfonylamino alcohols 7 The synthesis of γ-sulfonylamino alcohols 7 was performed according to a literature procedure starting from β-sulfonylamino esters 6. S1 The γ-sulfonylamino alcohols 7 were purified by recrystallization from diethyl ether. (R,S)-N-(3-Hydroxy-2-methyl-1-phenylpropyl)-4-methylbenzenesulfonamide (R,S)-anti- 7b. This compound is known in literature, but no spectral data are available. S2 White crystals, yield 63%. [α] D (c 0.1, CHCl 3 ). Mp C. IR (cm -1 ): ν max 1158, 1322, 3243, H NMR (300 MHz, CDCl 3 ): δ 0.76 (3H, d, J = 6.6 Hz), (1H, m), 2.33 (3H, s), 2.60 (1H, m), (1H, m), (1H, m), 4.17 (1H, d x d, J = 7.7, 7.7 Hz), 6.14 (1H, d, J = 7.7 Hz), (2H, m), (5H, m), 7.48 (2H, d, J = 8.3 Hz). 13 C NMR S1 Raheem, I. T.; Jacobsen, E. N. Adv. Synth. & Cat. 2005, 347, S2 Enders, D.; Gries, J. Synthesis 2005, 20, S-18
19 (75 MHz, CDCl 3 ): δ 14.7, 21.5, 41.0, 61.6, 65.0, (2C), (2C), 127.3, (2C), (2C), 137.4, 140.1, MS (ES, neg. mode) m/z (%): 318 (M - H +, 100). Anal. Calcd for C 17 H 21 NO 3 S: C 63.92; H 6.63; N Found: C 63.78; H 6.44; N (S,S)-N-(3-Hydroxy-2-methyl-1-phenylpropyl)-4-methylbenzenesulfonamide (S,R)-N-(3-Hydroxy-2-methyl-1-phenylpropyl)-4-methylbenzenesulfonamide (S,R)-anti- 7b. This compound is known in literature, but no spectral data are available. S2 White crystals, yield 73%. [α] D (c 0.1, MeOH). Mp C. IR (cm -1 ): ν max 1088, 1158, 1322, 3246, H NMR (300 MHz, CDCl 3 ): δ 0.76 (3H, d, J = 6.6 Hz), (1H, m), 2.33 (3H, s), 2.64 (1H, m), (1H, m), (1H, m), 4.17 (1H, d x d, J = 7.7, 7.7 Hz), 6.18 (1H, d, J = 7.7 Hz), (2H, m), (5H, m), (2H, m). 13 C NMR (75 MHz, CDCl 3 ): δ 14.7, 21.5, 41.0, 61.7, 65.0, (2C), (2C), 127.3, (2C), (2C), 137.4, 140.1, MS (ES, neg. mode) m/z (%): 318 (M - H +, 100). Anal. Calcd for C 17 H 21 NO 3 S: C 63.92; H 6.63; N Found: C 63.88; H 6.48; N (S,S)-syn- 7b. White crystals, yield 87%. [α] D (1S,2S)-7b-syn (c 0.4, MeOH) vs (1R,2R)-7b-syn and +26,1 (c 1.0, MeOH) in Lit. S3 Mp C vs C in Lit. IR (cm - 1 ): ν max 1025, 1155, 3248, H NMR (300 MHz, CDCl 3 ): δ 0.72 (3H, d, J = 6.6 Hz), (1H, m), 2.28 (1H, br s), 2.31 (3H, s), (2H, m), 4.61 (1H, d x d, J = 9.4, 4.4 Hz), 5.84 (1H, d, J = 9.4 Hz), (2H, m), 7.05 (2H, d, J = 8.3 Hz), (3H, m), 7.53 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 11.7, 21.5, 41.3, 59.2, 64.8, (2C), (3C), (2C), (2C), 137.5, 138.6, MS (ES, pos. mode) m/z (%): S2 Enders, D.; Gries, J. Synthesis 2005, 20, S3 (a) Raheem, I. T.; Jacobsen, E. N. Adv. Synth. & Cat. 2005, 347, (b) Davis, F. A.; Reddy, G. V.; Liang, C. -H. Tetr. Lett. 1997, 38, S-19
20 320 (M + H +, 100). Anal. Calcd for C 17 H 21 NO 3 S: C 63.92; H 6.63; N Found: C 63.76; H 6.56; N (S,R)-N-(3-Hydroxy-2-methyl-1-(4-methoxyphenyl)propyl)-4-methylbenzenesulfonamide (S,R)-anti-7c. White crystals, yield 86%. [α] D (c 0.4, MeOH). Mp C. IR (cm -1 ): ν max 1031, 1156, 2958, H NMR (300 MHz, CDCl 3 ): δ 0.73 (3H, d, J = 7.2 Hz), (1H, m), 2.31 (3H, s), 3.58 (1H, br s), (1H, m), 3.70 (3H, s), (1H, m), 4.10 (1H, d x d, J = 8.8, 8.8 Hz), 6.58 (2H, d, J = 8.3 Hz), 6.62 (1H, d, J = 8.8 Hz), 6.87 (2H, d, J = 8.3 Hz), 7.03 (2H, d, J = 8.3 Hz), 7.47 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 14.7, 21.5, 41.1, 55.3, 61.2, 65.2, (2C), (2C), (2C), (2C), 132.2, 137.5, 142.9, MS (ES, neg. mode) m/z (%): 348 (M - H +, 100). Anal. Calcd for C 18 H 23 NO 4 S: C 61.87; H 6.63; N Found: C 61.76; H 6.54; N Synthesis of chiral N-tosylazetidines 8 The synthesis of N-tosylazetidines 8 was performed according to a literature procedure starting from γ-sulfonylamino alcohols 7. S2 The N-tosylazetidines 8 were purified by flash chromatography. (R,R)-3-Methyl-2-phenyl-1-tosylazetidine (R,R)-trans-8b. R f = 0.37 (petroleum ether/ Et 2 O 7:3). White crystals, yield 89%. [α] D (c 0.2, CHCl 3 ) vs (c 1.0, CHCl 3, ee > 99%) in Lit. S2 Mp C vs C in Lit. ee > 98%, HPLC Daicel Chiralcel OD- H column: Hexane (99.6%) / i-propanol (0.4%), 0.5 ml min -1, 35 C, t R ((S,S)-trans-8b) = min, t R ((R,R)-trans-8b) = min. 1 H NMR (300 MHz, CDCl 3 ): δ 0.98 (3H, d, J = S2 Enders, D.; Gries, J. Synthesis 2005, 20, S-20
21 6.6 Hz), (1H, m), 2.44 (3H, s), 3.33 (1H, t, J = 7.7 Hz), 3.91 (1H, t, J = 7.7 Hz), 4.35 (1H, d, J = 7.2 Hz), (7H, m), 7.68 (2H, d, J = 8.3 Hz). Anal. Calcd for C 17 H 19 NO 2 S: C 67.74; H 6.35; N Found: C 67.49; H 6.18; N All spectroscopic data were in good agreement with reported data. S24 (S,S)-3-Methyl-2-phenyl-1-tosylazetidine (S,S)-trans-8b. R f = 0.13 (petroleum ether/ Et 2 O 8:2). White crystals, yield 94%. [α] D (c 0.3, CHCl 3 ) vs (c 1.0, CHCl 3, ee = 97%) in Lit. S2 Mp C vs C in Lit. ee > 98%, HPLC Daicel Chiralcel OD- H column: Hexane (99.6%) / i-propanol (0.4%), 0.5 ml min -1, 35 C, t R ((S,S)-trans-8b) = min, t R ((R,R)-trans-8b) = min. 1 H NMR (300 MHz, CDCl 3 ): δ 0.97 (3H, d, J = 7.2 Hz), (1H, m), 2.44 (3H, s), 3.33 (1H, t, J = 7.7 Hz), 3.91 (1H, t, J = 7.7 Hz), 4.35 (1H, d, J = 7.2 Hz), (7H, m), 7.68 (2H, d, J = 8.3 Hz). Anal. Calcd for C 17 H 19 NO 2 S: C 67.74; H 6.35; N Found: C 67.62; H 6.22; N All spectroscopic data were in good agreement with reported data. S2 (S,S)-3-Methyl-2-(4-methoxyphenyl)-1-tosylazetidine (S,S)-trans-8c. R f = 0.18 (petroleum ether/ Et 2 O 7:3). White crystals, yield 74%. [α] D (c 0.3, CHCl 3 ). Mp C. IR (cm -1 ): ν max 1152, 1335, 1515, H NMR (300 MHz, CDCl 3 ): δ 0.95 (3H, d, J = 6.6 Hz), (1H, m), 2.44 (3H, s), 3.27 (1H, t, J = 7.7 Hz), 3.79 (3H, s), 3.88 (1H, t, J = 7.7 Hz), 4.27 (1H, d, J = 7.7 Hz), 6.86 (2H, d, J = 8.3 Hz), (4H, m), 7.67 (2H, d, J = 8.3 Hz). 13 C NMR (75 MHz, CDCl 3 ): δ 17.6, 21.7, 35.3, 54.5, 55.4, 73.1, (2C), (2C), (2C), (2C), 132.2, 132.3, 143.9, MS (ES, pos. mode) m/z (%): 332 (M + H +, 100). Anal. Calcd for C 18 H 21 NO 3 S: C 65.23; H 6.39; N Found: C 64.94; H 6.15; N S2 Enders, D.; Gries, J. Synthesis 2005, 20, S-21
22 III. Copies of 1 H NMR and 13 C NMR spectra of 3, 4, 5, 6, 7 and 8 1 H NMR (300 MHz, CDCl 3 ) N S O Cl (R S,S,R)-anti-3a S-22
23 13 C NMR (75 MHz, CDCl 3 ) N S O Cl (R S,S,R)-anti-3a S-23
24 1 H NMR (300 MHz, CDCl 3 ) S N O Cl (R S,R,S)-anti-3a S-24
25 13 C NMR (75 MHz, CDCl 3 ) S N O Cl (R S,R,S)-anti-3a S-25
26 1 H NMR (300 MHz, CDCl 3 ) N S O Cl (R S,S,S)-syn-3a S-26
27 13 C NMR (75 MHz, CDCl 3 ) N S O Cl (R S,S,S)-syn-3a S-27
28 1 H NMR (300 MHz, CDCl 3 ) S N O (R S,S,R)-anti-3b S-28
29 13 C NMR (75 MHz, CDCl 3 ) S N O (R S,S,R)-anti-3b S-29
30 1 H NMR (300 MHz, CDCl 3 ) S N O (R S,R,S)-anti-3b S-30
31 13 C NMR (75 MHz, CDCl 3 ) S N O (R S,R,S)-anti-3b S-31
32 1 H NMR (300 MHz, CDCl 3 ) S N O (R S,S,S)-syn-3b S-32
33 13 C NMR (75 MHz, CDCl 3 ) S N O (R S,S,S)-syn-3b S-33
34 1 H NMR (300 MHz, CDCl 3 ) N S O MeO (R S,S,R)-anti-3c S-34
35 13 C NMR (75 MHz, CDCl 3 ) N S O MeO (R S,S,R)-anti-3c S-35
36 1 H NMR (300 MHz, CDCl 3 ) N S O MeO (R S,R,S)-anti-3c S-36
37 13 C NMR (75 MHz, CDCl 3 ) N S O MeO (R S,R,S)-anti-3c S-37
38 1 H NMR (300 MHz, CDCl 3 ) N S O MeO (R S,S,S)-syn-3c S-38
39 13 C NMR (75 MHz, CDCl 3 ) N S O MeO (R S,S,S)-syn-3c S-39
40 1 H NMR (300 MHz, CDCl 3 ).HCl Cl (S,R)-anti-4a S-40
41 13 C NMR (75 MHz, CDCl 3 ).HCl Cl (S,R)-anti-4a S-41
42 1 H NMR (300 MHz, CDCl 3 ).HCl Cl (R,S)-anti-4a S-42
43 13 C NMR (75 MHz, CDCl 3 ).HCl Cl (R,S)-anti-4a S-43
44 1 H NMR (300 MHz, CDCl 3 ).HCl (S,R)-anti-4b S-44
45 13 C NMR (75 MHz, CDCl 3 ).HCl (S,R)-anti-4b S-45
46 1 H NMR (300 MHz, CDCl 3 ).HCl (R,S)-anti-4b S-46
47 13 C NMR (75 MHz, CDCl 3 ).HCl (R,S)-anti-4b S-47
48 1 H NMR (300 MHz, CDCl 3 ).HCl (S,S)-syn-4b S-48
49 13 C NMR (75 MHz, CDCl 3 ).HCl (S,S)-syn-4b S-49
50 1 H NMR (300 MHz, CDCl 3 ).HCl MeO (S,R)-anti-4c S-50
51 13 C NMR (75 MHz, CDCl 3 ).HCl MeO (S,R)-anti-4c S-51
52 1 H NMR (300 MHz, CDCl 3 ).HCl MeO (R,S)-anti-4c S-52
53 13 C NMR (75 MHz, CDCl 3 ).HCl MeO (R,S)-anti-4c S-53
54 1 H NMR (300 MHz, CDCl 3 ) O 2 Cl (S,R)-anti-5a S-54
55 13 C NMR (75 MHz, CDCl 3 ) O 2 Cl (S,R)-anti-5a S-55
56 1 H NMR (300 MHz, CDCl 3 ) O 2 Cl (R,S)-anti-5a S-56
57 13 C NMR (75 MHz, CDCl 3 ) O 2 Cl (R,S)-anti-5a S-57
58 1 H NMR (300 MHz, CDCl 3 ) O 2 (S,R)-anti-5b S-58
59 13 C NMR (75 MHz, CDCl 3 ) O 2 (S,R)-anti-5b S-59
60 1 H NMR (300 MHz, CDCl 3 ) O 2 (R,S)-anti-5b S-60
61 13 C NMR (75 MHz, CDCl 3 ) O 2 (R,S)-anti-5b S-61
62 1 H NMR (300 MHz, DMSO-d 6 ) O 2 MeO (S,R)-anti-5c S-62
63 13 C NMR (75 MHz, DMSO-d 6 ) O 2 MeO (S,R)-anti-5c S-63
64 1 H NMR (300 MHz, DMSO-d 6 ) O 2 MeO (R,S)-anti-5c S-64
65 13 C NMR (75 MHz, DMSO-d 6 ) O 2 MeO (R,S)-anti-5c S-65
66 1 H NMR (300 MHz, CDCl 3 ) O Cl (S,R)-anti-6a S-66
67 13 C NMR (75 MHz, CDCl 3 ) O Cl (S,R)-anti-6a S-67
68 1 H NMR (300 MHz, CDCl 3 ) O Cl (R,S)-anti-6a S-68
69 13 C NMR (75 MHz, CDCl 3 ) O Cl (R,S)-anti-6a S-69
70 1 H NMR (300 MHz, CDCl 3 ) O (S,R)-anti-6b S-70
71 13 C NMR (75 MHz, CDCl 3 ) O (S,R)-anti-6b S-71
72 1 H NMR (300 MHz, CDCl 3 ) O (R,S)-anti-6b S-72
73 13 C NMR (75 MHz, CDCl 3 ) O (R,S)-anti-6b S-73
74 1 H NMR (300 MHz, CDCl 3 ) O (S,S)-syn-6b S-74
75 13 C NMR (75 MHz, CDCl 3 ) O (S,S)-syn-6b S-75
76 1 H NMR (300 MHz, CDCl 3 ) O MeO (S,R)-anti-6c S-76
77 13 C NMR (75 MHz, CDCl 3 ) O MeO (S,R)-anti-6c S-77
78 1 H NMR (300 MHz, CDCl 3 ) O MeO (R,S)-anti-6c S-78
79 13 C NMR (75 MHz, CDCl 3 ) O MeO (R,S)-anti-6c S-79
80 1 H NMR (300 MHz, CDCl 3 ) OH (R,S)-anti-7b S-80
81 13 C NMR (75 MHz, CDCl 3 ) OH (R,S)-anti-7b S-81
82 1 H NMR (300 MHz, CDCl 3 ) OH (S,R)-anti-7b S-82
83 13 C NMR (75 MHz, CDCl 3 ) OH (S,R)-anti-7b S-83
84 1 H NMR (300 MHz, CDCl 3 ) OH (S,S)-syn-7b S-84
85 13 C NMR (75 MHz, CDCl 3 ) OH (S,S)-syn-7b S-85
86 1 H NMR (300 MHz, CDCl 3 ) OH MeO (S,R)-anti-7c S-86
87 13 C NMR (75 MHz, CDCl 3 ) OH MeO (S,R)-anti-7c S-87
88 1 H NMR (300 MHz, CDCl 3 ) N (R,R)-trans-8b S-88
89 1 H NMR (300 MHz, CDCl 3 ) N (S,S)-trans-8b S-89
90 1 H NMR (300 MHz, CDCl 3 ) N MeO (S,S)-trans-8c S-90
91 13 C NMR (75 MHz, CDCl 3 ) N MeO (S,S)-trans-8c S-91
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