Chiral Brønsted Acid Catalyzed Enantioselective Intermolecular Allylic Aminations. Minyang Zhuang and Haifeng Du*
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- Αελλα Ἀλκμήνη Δασκαλοπούλου
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1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Chiral Brønsted Acid Catalyzed Enantioselective Intermolecular Allylic Aminations Minyang Zhuang and Haifeng Du* Beijing National Laboratory of Molecular Sciences, CAS Key laboratory of Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences Beijing , China Supporting Information S1
2 General consideration: All the solvents were purified under standard method. 1 H, 13 C, 19 F, and 31 P NMR spectra were recorded in CDCl 3 solution on Bruker AX-400 MHz instruments and spectral data were reported in ppm relative to tetramethylsilane (TMS) as internal standard. IR spectra were recorded on a Thermo Nicolet 6700 spectrometer. High-resolution mass spectralanalysis (HRMS) data were measured on the Thermo Exactive by means of the ESI technique. Ee s were determined by high performance liquid chromatography (HPLC) analysis. All the amine nucleophiles were used directly after purchase. General procedure for the synthesis of Allylic alcohols: allylic alcohols were prepared according to the reported method. To a stirred solution of, -unsaturated ketone chalcone (10 mmol) in methanol (25 ml) was added CeCl 3 7H 2 O (3.73 g, 10 mmol), the solution was cooled to 0 C and NaBH 4 (0.418 g, 11 mmol) was added. The mixture was stirred at room temperature for 1 h before water was added and exacted with CH 2 Cl 2. The combined organic phases were dried with Na 2 SO 4, and the solvents evaporated under vacuum. The pure compound was obtained after flash chromatography on silica gel. P. N. Chatterjee and S. Roy, Tetrahedron, 2012, 68, Typical procedure for the synthesis of chiral sulfonamides from allylic alcohol (Table 2, entry 1): To a dried Schlenk flask was added (E)-1,3-diphenylpropenol (1a) (0.084 g, 0.40 mmol), toluene sulfonamide (3) ( g, 0.60 mmol), and CHCl 3 (1.0 ml) under Ar. The reaction mixture was stirred at -60 C for 10 min before addition of chiral phosphoramide 2g ( g, 0.04 mmol). The reaction mixture was stirred at -60 ºC for 10 h and quenched with saturated NaHCO 3. The organic phase was directly purified by flash chromatography on silica gel (CH 2 Cl 2 ) to afford the desired product 4a as a white solid. S2
3 Typical procedure for the determination of the structures of regioisomers (4i and 4i ): To a solution of 4i and 4i ( g, 0.19 mmol) in a mixed solvent CCl 4 /CH 3 CN/H 2 O (1:1:1.6, v/v/v, 1.1 ml), NaIO 4 (0.165 g, 0.77 mmol) was added and stirred for 10 min. Then RuCl 3 H 2 O ( g, mmol) was added, and the mixture was stirred for 24 h at room temperature and quenched with 1N HCl. The mixture was extracted with CH 2 Cl 2, filtered with celite, concentrated and used directly for the GC-MS analysis. C.-Y. Zhou, S.-F. Zhu, L.-X. Wang and Q.-L. Zhou, J. Am. Chem. Soc., 2010, 132, (S)-(+)-[3,3 -Bis(diphenylmethyl)-1,1 -binaphthalen-2,2 -yl)-n-triflylphosphoramide: Yellow solid; m.p ºC; [α] 20 D (c 1.03, CH 2 Cl 2 ); IR (film) , , , , , cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.72 (t, J = 7.6 Hz, 2H), 7.50 (d, J = 5.0 Hz, 1H), (m, 4H), (m, 19H), (m, 4H), (m, 2H), 3.47 (brs, 1H); 31 P NMR (122 MHz, CDCl 3 ) δ -1.5; 19 F NMR (376 MHz, CDCl 3 ) δ -77.3; HRMS (FT-ICRMS) calcd for C 47 H 33 F 3 NO 5 PSNa (M+Na): , found: (E)-1,3-diphenylprop-2-en-1-ol (1a): 85% yield, white solid; 1 H NMR (400 MHz, CDCl 3 ) δ 7.42 (d, J = 7.2 Hz, 2H), 7.37 (t, J = 8.0 Hz, 4H), 7.30 (t, J = 7.6 Hz, 3H), (m, 1H), 6.68 (d, J = 15.8 Hz, 1H), 6.37 (dd, J = 15.8, 6.4 Hz, 1H), 5.37 (d, J = 6.4 Hz, 1H), 2.12 (brs, 1H); 13 C NMR S3
4 (100 MHz, CDCl 3 ) δ 143.0, 136.7, 131.7, 130.8, 128.8, 128.7, 128.0, 127.9, 126.8, 126.6, J. M. Dickinson, J. A. Murphy, C. W. Patterson and N. F. Wooster, J. Chem. Soc., Perkin Trans. 1, 1990, 1179; (E)-1,3-bis(4-fluorophenyl)prop-2-en-1-ol (1b): 61% yield, colorless oil; IR (film) 3371, 1602, 1508, 1227, 1157, 1085 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 4H), (m, 4H), 6.52 (d, J = 16.0 Hz, 1H), 6.18 (dd, J = 16.0, 6.0 Hz, 1H), 5.24 (d, J = 6.0 Hz, 1H), 2.99 (brs, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ (d, J = Hz), (d, J = Hz), (d, J = 3.0 Hz), (d, J = 3.0 Hz), (d, J = 2.0 Hz), 129.6, (d, J = 9.0 Hz), (d, J = 8.0 Hz), (d, J = 12.0 Hz), (d, J = 12.0 Hz), 74.4; HRMS (FT-ICRMS) calcd for C 15 H 11 F 2 O (M-H): , found: (E)-1,3-bis(4-chlorophenyl)prop-2-en-1-ol (1c): 72% yield, white solid; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 4H), (m, 4H), 6.55 (d, J = 16.0 Hz, 1H), 6.24 (dd, J = 16.0, 6.4 Hz, 1H), 5.27 (d, J = 6.4 Hz, 1H), 2.61 (brs, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 141.1, 134.9, 133.7, 131.8, 129.8, 128.9, 128.0, 127.9, P. N. Chatterjee and S. Roy, Tetrahedron, 2012, 68, S4
5 (E)-1,3-bis(4-bromophenyl)prop-2-en-1-ol (1d): 89% yield, white solid; 1 H NMR (400 MHz, CDCl 3 ) δ 7.49 (d, J = 6.8, 2H), 7.43 (d, J = 6.8, 2H), 7.29 (d, J = 8.4 Hz, 2H), 7.23 (d, J = 6.8 Hz, 2H), 6.59 (d, J = 16.0 Hz, 1H), 6.30 (dd, J = 16.0, 6.4 Hz, 1H), (m, 1H), 2.15 (d, J = 3.6 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 141.7, 135.5, 132.0, 132.0, 130.0, 128.4, 128.3, 122.0, P. N. Chatterjee and S. Roy, Tetrahedron, 2012, 68, (E)-1,3-di-p-tolylprop-2-en-1-ol (1e): 81% yield, white solid; 1 H NMR (400 MHz, CDCl 3 ) δ 7.24 (d, J =8.0 Hz, 4H), 7.20 (d, J = 8.0 Hz, 4H), 7.10 (d, J = 8.0 Hz, 2H), 7.05 (d, J = 8.0 Hz, 2H), 6.54 (d, J = 14.6 Hz, 1H), 6.24 (dd, J = 14.6, 6.4 Hz, 1H), 5.21 (d, J = 6.4 Hz, 1H), 2.63 (brs, 1H), 2.30 (s, 3H), 2.28 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 140.2, 137.5, 137.4, 134.0, 130.9, 130.3, 129.3, 129.3, 126.6, 126.5, 75.0, 21.3, P. N. Chatterjee and S. Roy, Tetrahedron, 2012, 68, (E)-1,3-di-m-tolylprop-2-en-1-ol (1f): 79% yield, colorless oil; IR (film) 3348, 1605, 1487, 1455, 1081 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 6H), 7.06 (d, J = 7.2 Hz, 1H), 7.02 (d, J = S5
6 6.0 Hz, 1H), 6.59 (d, J = 15.8 Hz, 1H), 6.28 (dd, J = 15.8, 6.4 Hz, 1H), 5.25 (d, J = 6.4 Hz, 1H), 2.44 (brs, 1H), 2.32 (s, 3H), 2.29 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 143.0, 138.4, 138.2, 136.7, 131.6, 130.6, 128.7, 128.6, 128.6, 128.6, 127.5, 127.2, 124.0, 123.6, 75.2, 21.6, 21.5; HRMS (FT-ICRMS) calcd for C 17 H 17 O (M-H): , found: (E)-1,3-di-o-tolylprop-2-en-1-ol (1g): 80% yield, colorless oil; IR (film) 3336, 1602, 1486, 1460, 1011 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.52 (d, J = 7.6 Hz, 1H), (m, 1H), (m, 6H), 6.86 (d, J = 16.0 Hz, 1H), 6.22 (dd, J = 16.0, 6.0 Hz, 1H), 5.57 (d, J = 6.0 Hz, 1H), 2.39 (s, 3H), 2.33 (s, 3H), 2.10 (brs, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 140.9, 135.9, 135.8, 135.4, 132.3, 130.8, 130.5, 128.7, 127.8, 126.6, 126.3, 126.0, 126.0, 72.3, 20.0, 19.4; HRMS (FT-ICRMS) calcd for C 17 H 17 O (M-H): , found: (E)-1,3-di(naphthalen-1-yl)prop-2-en-1-ol (1h): 65% yield, yellow oil; 1 H NMR (400 MHz, CDCl 3 ) δ 8.34 (d, J = 8.4 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), 7.70 (t, J = 7.2 Hz, 2H), (m, 7H), 7.41 (t, J = 8.0 Hz, 1H), 6.63 (dd, J = 15.6, 5.6 Hz, 1H), (m, 1H), 2.35 (d, J = 4.0 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 138.5, 134.6, 134.4, 134.3, 133.8, 131.4, 131.0, 129.1, 128.9, 128.7, 128.4, 128.3, 126.5, 126.3, 126.0, 126.0, 125.8, 125.7, 124.4, 124.2, 124.0, 124.0, K. Itoh, T. Ikeda, S. Tazuke and T. Shibatal, J. Phys. Chem., 1992, 96, S6
7 (E)-3-(4-chlorophenyl)-1-(p-tolyl)prop-2-en-1-ol (1i): 73% yield, white solid; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 6H), 7.18 (d, J = 8.0 Hz, 2H), 6.63 (d, J = 15.8 Hz, 1H), 6.35 (dd, J = 15.8, 6.2 Hz, 1H), (m, 1H), 2.35 (s, 3H), 2.00 (d, J = 3.0 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 139.9, 138.0, 135.4, 133.5, 132.5, 129.6, 129.2, 128.9, 128.0, 126.5, 75.1, P. N. Chatterjee and S. Roy, Tetrahedron, 2012, 68, (E)-3-(3-chlorophenyl)-1-(p-tolyl)prop-2-en-1-ol (1j): 83% yield, colorless oil; IR (film) 3342, 1594, 1566, 1512, 1426 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.27 (s, 1H), (m, 2H), (m, 5H), 6.49 (d, J = 15.8 Hz, 1H), 6.31 (dd, J = 15.8, 6.2 Hz, 1H), 5.21 (d, J = 6.2 Hz, 1H), 2.98 (brs, 1H), 2.30 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 139.7, 138.7, 137.7, 134.5, 133.3, 129.8, 129.4, 128.7, 127.7, 126.6, 126.5, 124.9, 74.7, 21.3; HRMS (FT-ICRMS) calcd for C 16 H 14 ClO (M-H): , found: (E)-1-(3-chlorophenyl)-3-(p-tolyl)prop-2-en-1-ol (1k): 77% yield, colorless oil; IR (film) 3339, 1596, 1574, 1512, 1428, 1188 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.33 (s, 1H), (m, 5H), S7
8 (m, 2H), 6.49 (d, J = 15.8 Hz, 1H), 6.14 (dd, J = 15.8, 6.8 Hz, 1H), 5.14 (d, J = 6.8 Hz, 1H), 3.27 (brs, 1H), 2.27 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 145.1, 137.9, 134.4, 133.5, 131.2, 129.9, 129.4, 127.7, 126.7, 126.5, 124.6, 74.5, 21.3; HRMS (FT-ICRMS) calcd for C 16 H 14 ClO (M-H): , found: (E)-3-(3-chlorophenyl)-1-phenylprop-2-en-1-ol (1l): 88%, colorless oil; IR (film) 3338, 1594, 1565, 1453, 1094, 1076 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 6H), (m, 3H), 6.57 (d, J = 16.0 Hz, 1H), 6.33 (dd, J = 16.0, 6.4 Hz, 1H), (m, 1H), 2.47 (brs, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 142.6, 138.6, 134.7, 133.2, 129.9, 129.1, 128.9, 128.1, 127.8, 126.7, 126.5, 125.0, 75.0; HRMS (FT-ICRMS) calcd for C 15 H 12 ClO (M-H): , found: (E)-3-(3-bromophenyl)-1-(p-tolyl)prop-2-en-1-ol (1m): 75% yield, white solid; IR (film) 3340, 1590, 1562, 1473, 1072 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.45 (s, 1H), 7.30 (d, J = 8.0 Hz, 1H), (m, 3H), (m, 3H), 6.50 (d, J = 16.0 Hz, 1H), 6.29 (dd, J = 16.0, 6.0 Hz, 1H), 5.24 (d, J = 6.0 Hz, 1H), 2.75 (brs, 1H), 2.31 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 139.7, 139.0, 137.7, 133.4, 130.6, 130.2, 129.5, 129.4, 128.6, 126.5, 125.4, 122.8, 74.7, 21.3; HRMS (FT-ICRMS) calcd for C 16 H 14 BrO (M-H): , found: S8
9 (E)-3-(2-bromophenyl)-1-(p-tolyl)prop-2-en-1-ol (1n): 67% yield, white solid; IR (film) 3355, 1512, 1466, 1436, 1022 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.51 (d, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.30 (d, J = 8.0 Hz, 2H), (m, 3H), (m, 2H), 6.28 (dd, J = 15.6, 6.4 Hz, 1H), (m, 1H), 2.36 (d, J = 3.2 Hz, 1H), 2.33 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 139.7, 137.7, 136.7, 134.9, 133.1, 129.5, 129.1, 127.6, 127.4, 126.5, 125.6, 124.0, 75.0, 21.3; HRMS (FT-ICRMS) calcd for C 16 H 14 BrO (M-H): , found: (E)-3-(2,6-dichlorophenyl)-1-(p-tolyl)prop-2-en-1-ol (1o): 80% yield, white solid; IR (film) 3294, 1555, 1512, 1428, 1180, 1090 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.37 (d, J = 8.0 Hz, 2H), 7.30 (d, J = 8.0 Hz, 2H), 7.20 (d, J = 8.0 Hz, 2H), 7.09 (t, J = 8.0 Hz, 1H), 6.74 (d, J = 16.0 Hz, 1H), 6.42 (dd, J = 16.0, 5.6 Hz, 1H), (m, 1H), 2.36 (s, 3H), 2.06 (d, J = 4.0 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 140.1, 139.4, 137.9, 134.7, 134.5, 129.6, 128.6, 128.4, 126.9, 124.0, 75.0, 21.4; HRMS (FT-ICRMS) calcd for C 16 H 13 Cl 2 O (M-H): , found: S9
10 (E)-3-(3-chlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-ol (1p): 66% yield, colorless oil; IR (film) 3339, 1602, 1509, 1224, 1078 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 3H), (m, 3H), (m, 2H), 6.53 (d, J = 16.0 Hz, 1H), 6.28 (dd, J = 16.0, 6.4 Hz, 1H), (m, 1H), 2.80 (brs, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ (d, J = Hz), 138.4, (d, J = 3.0 Hz), 134.7, 132.9, 130.0, 129.3, (d, J = 8.0 Hz), 128.0, 126.6, 125.0, (d, J = 21.0 Hz), 74.3; HRMS (FT-ICRMS) calcd for C 15 H 11 ClFO (M-H): , found: (E)-3-(3-bromophenyl)-1-(m-tolyl)prop-2-en-1-ol (1q): 73% yield, colorless oil; IR (film) 3339, 1562, 1474, 1072 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.53 (s, 1H), (m, 1H), (m, 6H), 6.61 (d, J = 15.6 Hz, 1H), 6.37 (dd, J = 15.6, 6.0 Hz, 1H), (m, 1H), 2.36 (s, 3H), 2.09 (d, J = 3.4 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 142.6, 139.0, 138.7, 133.3, 130.8, 130.3, 129.6, 129.0, 128.9, 128.8, 127.2, 125.5, 123.6, 123.0, 75.1, 21.7; HRMS (FT-ICRMS) calcd for C 16 H 14 BrO (M-H): , found: (E)-3-(3-bromophenyl)-1-(o-tolyl)prop-2-en-1-ol (1r): 79% yield, colorless oil; IR (film) 3326, 1590, 1562, 1473, 1072 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 1H), (m, 5H), 6.56 (d, J = 16.0 Hz, 1H), 6.37 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), 2.37 (s, 3H), 2.06 (d, J = 3.4 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 140.5, 139.0, 135.5, 132.5, 130.9, 130.8, 130.3, 129.6, 129.1, 128.0, 126.7, 126.1, 125.4, 123.0, 71.8, 19.4; HRMS (FT-ICRMS) calcd for C 16 H 14 BrO (M-H): , found: S10
11 (E)-N-(1,3-diphenylallyl)-4-methoxybenzenesulfonamide(Table 1, entry 12): White solid; yield: 72%; [α] 20 D (c 0.82, CH 2 Cl 2 ) (72% ee); 1 H NMR (400 MHz, CDCl 3 ) δ 7.69 (d,j = 8.8 Hz, 2H), (m,10h), 6.78(d,J = 8.8 Hz, 2H), 6.35 (d, J = 15.6 Hz, 1H), 6.07 (dd, J = 15.6, 6.6 Hz, 1H), (m,2h), 3.74 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 162.9, 139.8, 136.3, 132.5, 132.3, 129.6, 128.9, 128.7, 128.4, 128.1, 128.0, 127.3, 126.7, 114.2, 60.0, P. Trillo, A. Baeza and C. Nájera, Eur. J. Org. Chem., 2012, (E)-N-(1,3-diphenylallyl)-N-methylbenzenesulfonamide(Table 1, entry 13):Colorless oil; yield: 93%; [α] 20 D -0.5 (c0.98, CH 2 Cl 2 ) (2% ee); IR (film) 3060, 1447, 1339, 1164, 1088 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.83 (d,j = 8.6 Hz, 2H), (m,1h), (m,2h), (m, 10H), 6.40 (d, J = 16.0 Hz, 1H), 6.16 (dd, J = 16.0, 7.4 Hz, 1H), 5.87 (d, J = 7.4 Hz, 1H), 2.71 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ139.7, 138.6, 136.3, 134.9, 132.6, 129.1, 128.8, 128.3, 128.1, 128.0, 127.6, 126.7, 124.2, 62.6, 30.4; HRMS (ESI) calcd for C 22 H 21 NO 2 SNa (M+Na): , found: S11
12 (E)-N-(1,3-diphenylallyl)benzenesulfonamide(Table 1, entry 14): White solid; yield: 78%; [α] 20 D -19.9(c0.96, CH 2 Cl 2 ) (72% ee); 1 H NMR (400 MHz, CDCl 3 ) δ 7.77 (d,j = 8.0 Hz, 2H), (m,1h), (m,2h), (m, 10H), 6.38 (d, J = 15.8 Hz, 1H), 6.06 (dd, J = 15.8, 6.4 Hz, 1H), (m,2h); 13 C NMR (100 MHz, CDCl 3 ) δ140.9, 139.7, 136.2, 132.6, 132.4, 129.0, 128.9, 128.7, 128.4, 128.2, 128.1, 127.2, 126.7, G.-W. Wang, Y.-B. Shen and X.-L. Wu, Eur. J. Org. Chem., 2008, (E)-N-(1,3-diphenylallyl)-2,4,6-triisopropylbenzenesulfonamide(Table 1, entry 15): White solid; yield: 82%; m.p ºC;[α] 20 D -22.4(c0.78, CH 2 Cl 2 ) (84% ee); IR (film) 3300, 1600, 1455, 1425, 1321, 1151 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m,4h), (m,4h), (m,2h), 7.09 (s, 2H), 6.39 (d, J = 15.8 Hz, 1H), 6.10 (dd, J = 15.8, 6.6 Hz, 1H), 5.19 (dd, J = 6.6, 6.0 Hz, 1H), 4.75 (d, J = 6.0 Hz, 1H), (m, 2H), (m, 1H), 1.25 (s, 3H), 1.24 (s, 3H), 1.23 (s, 3H), 1.21 (s, 3H), 1.15 (s, 3H), 1.14 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ152.9, 150.1, 140.2, 136.3, 134.0, 132.2, 129.0, 128.7, 128.6, 128.2, 128.1, 127.4, 126.7, 123.8, 59.9, 34.3, 30.0, 25.2, 24.8, 23.8, 23.7; HRMS (ESI) calcd for C 30 H 37 NO 2 SNa (M+Na): , found: S12
13 N-[1,3-diphenyl-(E)-2-propenyl]-4-methylbenzenesulfonamide (4a) (Table 2, entry 1): White solid; yield: 88%; [α] D (c 0.98, CH 2 Cl 2 ) (75% ee) ([α] D (c 1.0, CHCl 3 ), 95% ee for R); 1 H NMR (400 MHz, CDCl 3 ) δ 7.65 (d, J = 8.2 Hz, 2H), (m, 12H), 6.35 (d, J = 15.8 Hz, 1H), 6.07 (dd, J = 15.8, 6.8 Hz, 1H), 5.11 (dd, J = 7.0, 6.8 Hz, 1H), 4.97 (d, J = 7.0 Hz, 1H), 2.32 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 143.5, 139.9, 138.0, 136.3, 132.4, 129.7, 129.0, 128.7, 128.4, 128.1, 128.0, 127.6, 127.3, 126.7, 60.0, Bower, J. F., Jumnah,R., Williams, A. C. and Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1, 1997, (E)-N-(1,3-bis(4-fluorophenyl)allyl)-4-methylbenzenesulfonamide (4b) (Table 2, entry 2): White solid; yield: 82%; m.p ºC; [α] 20 D (c 1.04, CH 2 Cl 2 ) (70% ee); IR (film) 3269, 1601, 1509, 1158 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.64 (d, J = 8.2 Hz, 2H), (m, 6H), (m, 4H), 6.28 (d, J = 15.8 Hz, 1H), 5.98 (dd, J = 15.8, 6.8 Hz, 1H), 5.69 (d, J = 7.6 Hz, 1H), 5.07 (dd, J = 7.6, 6.8 Hz, 1H), 2.31 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ (d, J = Hz), (d, J = Hz), 143.4, 137.8, (d, J = 3 Hz), (d, J = 4 Hz), 131.1, 129.6, (d, J = 8 Hz), (d, J = 8 Hz), 127.9, 127.4, (d, J = 9 Hz), (d, J = 10 Hz), 59.2, 21.5; HRMS (FT-ICRMS) calcd for C 22 H 19 F 2 NO 2 SNa (M+Na): , found: S13
14 (E)-N-(1,3-bis(4-chlorophenyl)allyl)-4-methylbenzenesulfonamide (4c) (Table 2, entry 3): White solid; yield: 61%; m.p ºC; [α] 20 D (c 1.00, CH 2 Cl 2 ) (85% ee); IR (film) 3270, 1490, 1324, 1159 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.62 (d, J = 8.2 Hz, 2H), (m, 10H), 6.26 (d, J = 15.8 Hz, 1H), 6.02 (dd, J = 15.8, 6.6 Hz, 1H), (m, 1H), (m, 1H), 2.32 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 143.7, 138.1, 137.7, 134.6, 133.9, 133.8, 131.3, 129.7, 129.0, 128.8, 128.7, 128.5, 127.9, 127.4, 59.3, 21.6; HRMS (FT-ICRMS) calcd for C 22 H 19 Cl 2 NO 2 SNa (M+Na): , found: (E)-N-(1,3-bis(4-bromophenyl)allyl)-4-methylbenzenesulfonamide (4d) (Table 2, entry 4): White solid; yield: 60%; m.p ºC; [α] 20 D -8.3 (c 0.96, CH 2 Cl 2 ) (86% ee); IR (film) 3261, 1487, 1321, 1158 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.60 (d, J = 8.4 Hz, 2H), (m, 4H), 7.14 (d, J = 8.0 Hz, 2H), 7.03 (d, J = 8.4 Hz, 4H), 6.27 (d, J = 15.8 Hz, 1H), 6.04 (dd, J = 15.8, 6.8 Hz, 1H), 5.26 (d, J = 7.2 Hz, 1H), 5.05 (dd, J = 7.2, 6.8 Hz, 1H), 2.35 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 143.8, 138.5, 137.7, 135.0, 132.0, 131.9, 131.6, 129.7, 129.0, 128.6, 128.3, 127.5, 122.2, 59.3, 21.7; HRMS (FT-ICRMS) calcd for C 22 H 19 Br 2 NO 2 SNa (M+Na): , found: (E)-N-(1,3-di-p-tolylallyl)-4-methylbenzenesulfonamide (4e) (Table 2, entry 5): White solid; S14
15 yield: 77%; m.p ºC; [α] 20 D (c 1.00, CH 2 Cl 2 ) (66% ee); IR (film) 3273, 1512, 1434, 1324, 1159 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.70 (d, J = 8.2 Hz, 2H), 7.19 (d, J = 8.0 Hz, 2H), (m, 8H), 6.35 (d, J = 15.8 Hz, 1H), 6.06 (dd, J = 15.8, 6.4 Hz, 1H), 5.11 (dd, J = 7.2, 6.4 Hz, 1H), 5.05 (d, J = 7.2 Hz, 1H), 2.38 (s, 3H), 2.36 (s, 3H), 2.35 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 143.3, 138.0, 137.9, 137.8, 137.1, 133.6, 132.0, 129.6, 129.5, 129.3, 127.5, 127.2, 126.6, 59.8, 21.6, 21.4, 21.2; HRMS (FT-ICRMS) calcd for C 24 H 25 NO 2 SNa (M+Na): , found: (E)-N-(1,3-di-m-tolylallyl)-4-methylbenzenesulfonamide (4f) (Table 2, entry 6): White solid; yield: 80%; m.p ºC; [α] 20 D (c 0.89, CH 2 Cl 2 ) (62% ee); IR (film) 3274, 1605, 1326, 1159, 1092 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.66 (d, J = 7.2 Hz, 2H), (m, 4H), (m, 6H), 6.33 (d, J = 16.0 Hz, 1H), 6.06 (dd, J = 16.0, 6.4 Hz, 1H), 5.07 (dd, J = 6.4, 6.4 Hz, 1H), 4.96 (brs, 1H), 2.34 (s, 3H), 2.31 (s, 3H), 2.25 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 143.4, 139.8, 138.6, 138.2, 138.1, 136.3, 132.3, 129.6, 128.8, 128.7, 128.6, 128.5, 128.3, 128.0, 127.6, 127.4, 124.3, 123.9, 60.0, 21.6, 21.5, 21.4; HRMS (FT-ICRMS) calcd for C 24 H 25 NO 2 SNa (M+Na): , found: (E)-N-(1,3-di-o-tolylallyl)-4-methylbenzenesulfonamide (4g) (Table 2, entry 7): White solid; yield: 80%; m.p ºC; [α] 20 D -7.5 (c 0.93, CH 2 Cl 2 ) (22% ee); IR (film) 3275, 1603, 1489, 1459, 1325, 1159, 1092 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.66 (d, J = 8.2 Hz, 2H), (m, S15
16 10H), 6.54 (d, J = 15.6 Hz, 1H), 5.99 (dd, J = 15.6, 6.4 Hz, 1H), 5.38 (dd, J = 7.2, 6.4 Hz, 1H), 5.30 (d, J = 7.2 Hz, 1H), 2.33 (s, 6H), 2.18 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 143.3, 138.0, 137.9, 135.7, 135.6, 135.4, 130.9, 130.3, 129.9, 129.6, 129.5, 127.9, 127.8, 127.3, 127.0, 126.5, 126.1, 125.9, 56.7, 21.6, 19.8, 19.4; HRMS (FT-ICRMS) calcd for C 24 H 25 NO 2 SNa (M+Na): , found: (E)-N-(1,3-di(naphthalen-1-yl)allyl)-4-methylbenzenesulfonamide (4h) (Table 2, entry 8): White solid; yield: 63%; m.p ºC; [α] 20 D -0.8 (c 0.80, CH 2 Cl 2 ) (18% ee); IR (film) 3274, 1597, 1510, 1326, 1157, 1091 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 8.16 (d, J = 6.8 Hz, 1H), (m, 5H), 7.66 (d, J = 8.2 Hz, 2H), (m, 8H), 7.24 (d, J = 15.0 Hz, 1H), 7.02 (d, J = 8.0 Hz, 2H), 6.37 (dd, J = 15.8, 6.0 Hz, 1H), 6.02 (dd, J = 7.2, 6.0 Hz, 1H), 5.44 (d, J = 7.2 Hz, 1H), 2.24 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 143.4, 137.9, 135.4, 134.2, 134.1, 133.7, 131.6, 131.2, 130.7, 129.9, 129.5, 129.1, 129.0, 128.6, 128.4, 127.4, 126.8, 126.3, 126.1, 126.0, 125.8, 125.6, 125.4, 124.1, 123.9, 123.6, 57.0, 21.5; HRMS (FT-ICRMS) calcd for C 30 H 25 NO 2 SNa (M+Na): , found: (E)-N-(3-(4-cholophenyl)-1-(p-tolyl)allyl)-4-methylbenzenesulfonamide (4i) and (E)-N-(1-(4- chlorophenyl)-3-(p-tolyl)allyl)-4-methylbenzenesulfonamide (4i ) (Table 3, entry 1): White S16
17 solid; yield: 68%; m.p ºC; [α] 20 D (c 1.01, CH 2 Cl 2 ) (4i/4i = 4.3:1, major product 4i 82% ee, minor product 4i 69% ee); IR (film) 3271, 1511, 1492, 1325, 1159, 1090 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) for major product 4i: δ 7.64 (d, J = 7.8 Hz, 2H), 7.18 (d, J = 7.8 Hz, 2H), (m, 8H), 6.29 (d, J = 15.8 Hz, 1H), 6.04 (dd, J = 15.8, 6.2 Hz, 1H), 5.42 (d, J = 6.8 Hz, 1H), 5.03 (dd, J = 6.8, 6.2 Hz, 1H), 2.30 (s, 3H), 2.27 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) for major product 4i: δ 143.4, 137.9, 137.8, 136.6, 134.9, 133.5, 130.6, 130.0, 129.4, 128.7, 127.9, 127.5, 127.1, 126.6, 59.7, 21.6, 21.2; HRMS (FT-ICRMS) calcd for C 23 H 22 NO 2 ClSNa (M+Na): , found: (E)-N-(3-(m-chlorophenyl)-1-(p-tolyl)allyl)-4-methylbenzenesulfonamide (4j) and (E)-N-(1- (m-chlorophenyl)-3-(p-tolyl)allyl)-4-methylbenzenesulfonamide (4j ) (Table 3, entry 2): White solid; yield: 70%; m.p ºC; [α] 20 D (c 1.01, CH 2 Cl 2 ) (4j/4j = 8:1, major product 4j 66% ee); IR (film) 3270, 1595, 1430, 1324, 1158, 1092 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) for major product 4j: δ 7.66 (d, J = 7.6 Hz, 2H), (m, 4H), (m, 6H), 6.27 (d, J = 15.8 Hz, 1H), 6.05 (dd, J = 15.8, 6.4 Hz, 1H), (m, 1H), 5.05 (dd, J = 6.4, 6.4 Hz, 1H), 2.33 (s, 3H), 2.28 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) for major product 4j: δ 143.5, 138.3, 138.0, 136.5, 134.5, 130.6, 130.2, 129.8, 129.6, 127.9, 127.5, 127.1, 126.6, 125.0, 59.6, 21.6, 21.2; HRMS (FT-ICRMS) calcd for C 23 H 22 NO 2 ClSNa (M+Na): , found: (E)-N-(3-(3-chlorophenyl)-1-phenylallyl)-4-methylbenzenesulfonamide (4l) and (E)-N-(1-(3- S17
18 chlorophenyl)-3-phenylallyl)-4-methylbenzenesulfonamide (4l ) (Table 3, entry 4): White solid; yield: 56%; m.p ºC; [α] 20 D (c 0.98, CH 2 Cl 2 ) (4l/4l = 3.5:1, major product 4l 67% ee, minor product 4l 58% ee); IR (film) 3269, 1596, 1325, 1159, 1092 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) for major product 4l: δ 7.65 (d, J = 8.2 Hz, 2H), (m, 3H), (m, 6H), (m, 1H), (m, 1H), 6.28 (d, J = 16.0 Hz, 1H), 6.06 (dd, J = 16.0, 6.8 Hz, 1H), 5.34 (d, J = 7.4 Hz, 1H), 5.08 (dd, J = 7.4, 6.8 Hz, 1H), 2.32 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) for major product 4l: δ 143.6, 139.5, 138.2, 137.9, 134.6, 130.8, 130.0, 129.9, 129.7, 129.0, 128.2, 127.9, 127.5, 127.2, 126.6, 125.0, 59.8, 21.6; HRMS (FT-ICRMS) calcd for C 22 H 20 NO 2 ClSNa (M+Na): , found: (E)-N-(3-(3-bromophenyl)-1-(p-tolyl)allyl)-4-methylbenzenesulfonamide (4m) and (E)-N-(1- (3-bromophenyl)-3-(p-tolyl)allyl)-4-methylbenzenesulfonamide (4m ) (Table 3, entry 5): White solid; yield: 87%; m.p ºC; [α] 20 D (c 0.98, CH 2 Cl 2 ) (4m/4m = 6.7:1, major product 4m 76% ee, minor product 4m 70% ee); IR (film) 3269, 1594, 1324, 1158, 1092 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) for major product 4m: δ 7.66 (d, J = 8.2 Hz, 2H), 7.30 (d, J = 7.2 Hz, 1H), (m, 1H), 7.14 (d, J = 8.2 Hz, 2H), (m, 6H), 6.26 (d, J = 15.8 Hz, 1H), 6.04 (dd, J = 15.8, 6.6 Hz, 1H), (m, 1H), 5.05 (dd, J = 6.8, 6.6 Hz, 1H), 2.33 (s, 3H), 2.28 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) for major product 4m: δ 143.5, 138.5, 138.0, 136.5, 130.8, 130.5, 130.2, 130.1, 129.6, 129.5, 127.5, 127.1, 125.4, 122.7, 59.6, 21.6, 21.2; HRMS (FT-ICRMS) calcd for C 23 H 22 NO 2 BrSNa (M+Na): , found: S18
19 (E)-N-(3-(o-bromophenyl)-1-(p-tolyl)allyl)-4-methylbenzenesulfonamide (4n) and (E)-N-(1-(obromophenyl)-3-(p-tolyl)allyl)-4-methylbenzenesulfonamide (4n ) (Table 3, entry 6): White solid; yield: 87%; m.p ºC; [α] 20 D 1.3 (c 1.10, CH 2 Cl 2 ) (4n/4n = 3:1, major product 4n 13% ee, minor product 4n 94% ee); IR (film) 3271, 1600, 1512, 1436, 1325, 1159, 1092 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) for major product 4n: δ 7.69 (d, J = 7.6 Hz, 2H), 7.48 (d, J = 7.8 Hz, 1H), (m, 9H), 6.69 (d, J = 15.8 Hz, 1H), 6.01 (dd, J = 15.8, 7.0 Hz, 1H), (m, 1H), 5.06 (dd, J = 7.0, 6.8 Hz, 1H), (m, 6H); 13 C NMR (100 MHz, CDCl 3 ) for major product 4n: δ 143.4, 138.0, 136.6, 136.2, 132.9, 131.5, 130.7, 129.6, 129.4, 129.3, 129.2, 127.4, 127.3, 127.1, 126.6, 123.8, 59.7, 21.5, 21.2; HRMS (FT-ICRMS) calcd for C 23 H 22 NO 2 BrSNa (M+Na): , found: (E)-N-(3-(2,6-dichlorophenyl)-1-(p-tolyl)allyl)-4-methylbenzenesulfonamide (4o) and (E)-N-(1- (2,6-dichlorophenyl)-3-(p-tolyl)allyl)-4-methylbenzenesulfonamide (4o ) (Table 3, entry 7): White solid; yield: 16%; m.p ºC; [α] 20 D 1.8 (c 0.71, CH 2 Cl 2 ) (4o/4o > 20:1, major product 4o 60% ee); IR (film) 3274, 1557, 1428, 1324, 1159, 1092 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) for major product 4o: δ 7.76 (d, J = 8.2 Hz, 2H), (m, 2H), 7.24 (d, J = 8.0 Hz, 2H), 7.18 (d, J = 8.0 Hz, 2H), (m, 3H), 6.50 (d, J = 16.2 Hz, 1H), 6.28 (dd, J = 16.2, 6.0 Hz, 1H), 5.18 (dd, J = 7.2, 6.0 Hz, 1H), 5.01 (d, J = 7.2 Hz, 1H), 2.41 (s, 3H), 2.35 (s, 3H); 13 C NMR (100 MHz, S19
20 CDCl 3 ) for major product 4o: δ 143.5, 138.0, 137.9, 137.1, 136.5, 134.6, 133.9, 129.7, 129.6, 128.6, 127.5, 127.4, 125.8, 59.6, 21.7, 21.3; HRMS (FT-ICRMS) calcd for C 23 H 21 NO 2 Cl 2 SNa (M+Na): , found: (E)-N-(3-(3-chlorophenyl)-1-(4-fluorophenyl)allyl)-4-methylbenzenesulfonamide (4p) and (E)-N-(1-(3-chlorophenyl)-1-(3-fluorophenyl)allyl)-4-methylbenzenesul-fonamide (4p ) (Table 3, entry 8): White solid; yield: 63%; m.p ºC; [α] 20 D (c 0.98, CH 2 Cl 2 ) (4p/4p = 3:1, major product 4p 59% ee, minor product 4p 73% ee); IR (film) 3268, 1598, 1509, 1327, 1226, 1159, 1092cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) for major product 4p: δ 7.61 (d, J = 8.6 Hz, 2H), (m, 8H), (m, 2H), 6.25 (d, J = 15.8 Hz, 1H), 6.04 (dd, J = 15.8, 6.8 Hz, 1H), 5.41 (d, J = 7.4 Hz, 1H), 5.09 (dd, J = 7.4, 6.8 Hz, 1H), 2.34 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) for major product 4p: δ (d, J = 245 Hz), 143.8, (d, J = 17 Hz), (d, J = 3 Hz), 134.6, 131.1, 129.9, 129.7, (d, J = 6 Hz), (d, J = 8 Hz), 128.1, 127.5, 127.4, 126.6, 125.0, (d, J = 17 Hz), 59.1, 21.6; HRMS (FT-ICRMS) calcd for C 22 H 19 NO 2 ClFSNa (M+Na): , found: (E)-N-(3-(3-bromophenyl)-1-(m-tolyl)allyl)-4-methylbenzenesulfonamide (4q) and (E)-N-(1- S20
21 (3-bromophenyl)-3-(m-tolyl)allyl)-4-methylbenzenesulfonamide (4q ) (Table 3, entry 9): White solid; yield: 64%; m.p ºC; [α] 20 D (c 0.96, CH 2 Cl 2 ) (4q/4q = 6.9:1, major product 4q 76%, minor product 4q 53% ee); IR (film) 3270, 1594, 1562, 1426, 1327, 1159, 1092 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) for major product 4q: δ 7.65 (d, J = 8.2 Hz, 2H), 7.31 (d, J = 7.2 Hz, 1H), (m, 1H), (m, 5H), 7.01 (d, J = 7.4 Hz, 1H), 6.96 (d, J = 7.6 Hz, 1H), 6.92 (s, 1H), 6.27 (d, J = 15.8 Hz, 1H), 6.04 (dd, J = 15.8, 6.6 Hz, 1H), 5.37 (d, J = 7.2 Hz, 1H), 5.05 (dd, J = 7.2, 6.6 Hz, 1H), 2.33 (s, 3H), 2.22 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) for major product 4q: δ 143.5, 139.3, 138.7, 138.5, 137.9, 130.8, 130.5, 130.1, 129.6, 129.5, 128.9, 127.9, 127.5, 125.4, 124.2, 122.7, 59.8, 21.6, 21.5; HRMS (FT-ICRMS) calcd for C 23 H 22 NO 2 BrSNa (M+Na): , found: (E)-N-(3-(3-bromophenyl)-1-(o-tolyl)allyl)-4-methylbenzenesulfonamide (4r) and (E)-N-(1-(3- bromophenyl)-3-(o-tolyl)allyl)-4-methylbenzenesulfonamide (4r ) (Table 3, entry 10): White solid; yield: 52%; m.p ºC; [α] 20 D (c 0.81, CH 2 Cl 2 ) (4r/4r = 3.8:1, major product 4r 71% ee, minor product 4r 55% ee); IR (film) 3273, 1594, 1324, 1158, 1092 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) for major product 4r: δ 7.63 (d, J = 8.0 Hz, 2H), 7.30 (d, J = 7.6 Hz, 1H), (m, 9H), 6.18 (d, J = 15.8 Hz, 1H), 6.07 (dd, J = 15.8, 5.2 Hz, 1H), (m, 2H), 2.33 (s, 3H), 2.28 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) for major product 4r: δ 143.5, 138.5, 137.9, 137.4, 135.7, 131.0, 130.8, 130.4, 130.1, 129.8, 129.6, 129.5, 128.0, 137.4, 127.0, 126.6, 125.4, 122.7, 56.3, 21.6, 19.4; HRMS (FT-ICRMS) calcd for C 23 H 22 NO 2 BrSNa (M+Na): , found: S21
22 Table 1, entry 12 The chromatograms for determination of the enantiomeric excess HPLC Conditions:Column: ChiralcelOD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate:0.5 ml/min; Detection: UV 254 nm Racemic Chiral Table 1, entry 13 HPLC Conditions:Column: ChiralcelOD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate:0.5 ml/min; Detection: UV 254 nm Racemic Chiral S22
23 Table 1, entry 14 HPLC Conditions:Column: ChiralcelOD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate:0.5 ml/min; Detection: UV 254 nm Racemic Chiral Table 1, entry 15 HPLC Conditions:Column: ChiralpakAD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA (98/2 ); Flow rate:1 ml/min; Detection: UV 254 nm Racemic Chiral S23
24 Table 2, entry 1 HPLC Conditions: Column: Chiralcel OD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral Table 2, entry 2 HPLC Conditions: Column: Chiralcel OD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral S24
25 Table 2, entry 3 HPLC Conditions: Column: Chiralcel AS-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral Table 2, entry 4 HPLC Conditions: Column: Chiralpak AD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral S25
26 Table 2, entry 5 HPLC Conditions: Column: Chiralcel OD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral Table 2, entry 6 HPLC Conditions: Column: Chiralpak AD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 1.0 ml/min; Detection: UV 254 nm Racemic Chiral S26
27 Table 2, entry 7 HPLC Conditions: Column: Chiralpak AD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 1.0 ml/min; Detection: UV 254 nm Racemic Chiral Table 2, entry 8 HPLC Conditions: Column: Chiralpak AD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 0.5 ml/min; Detection: UV 310 nm Racemic Chiral S27
28 Table 3, entry 1 HPLC Conditions: Column: Chiralpak AD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 85/15 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral Table 3, entry 2 HPLC Conditions: Column: Chiralcel OD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral S28
29 Table 3, entry 4 HPLC Conditions: Column: Chiralcel AS-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral Table 3, entry 5 HPLC Conditions: Column: Chiralcel OD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral S29
30 Table 3, entry 6 HPLC Conditions: Column: Chiralcel OD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral Table 3, entry 7 HPLC Conditions: Column: Chiralpak AD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 90/10 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral S30
31 Table 3, entry 8 HPLC Conditions: Column: Chiralcel OD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 85/15 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral Table 3, entry 9 HPLC Conditions: Column: Chiralpak AD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 90/10 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral S31
32 Table 3, entry 10 HPLC Conditions: Column: Chiralpak AD-H, Daicel Chemical Industries, Ltd., Eluent: Hexanes/IPA ( 75/25 ); Flow rate: 0.5 ml/min; Detection: UV 254 nm Racemic Chiral S32
33 S33
34 S34
35 S35
36 S36
37 S37
38 S38
39 S39
40 S40
41 S41
42 S42
43 S43
44 S44
45 S45
46 S46
47 S47
48 S48
49 S49
50 S50
51 S51
52 S52
53 S53
54 S54
55 S55
56 S56
57 S57
58 S58
59 S59
60 S60
61 S61
62 S62
63 S63
64 S64
65 S65
66 S66
67 S67
68 S68
69 S69
70 S70
71 S71
72 S72
73 S73
74 S74
75 S75
76 S76
77 S77
78 S78
79 S79
80 S80
81 S81
82 S82
83 S83
84 S84
85 S85
86 S86
87 S87
88 S88
89 S89
90 S90
91 S91
92 S92
93 S93
94 S94
95 S95
96 S96
97 S97
98 S98
99 S99
100 S100
101 S101
102 S102
103 S103
104 S104
105 S105
106 S106
107 S107
108 S108
109 S109
110 S110
111 S111
112 S112
113 S113
114 S114
115 S115
116 S116
117 S117
118 S118
119 S119
120 S120
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