Supporting Information
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1 Supporting Information Palladium-Catalyzed Asymmetric Benzylic Substitution of Secondary Benzyl Carbonates with Nitrogen and Oxygen Nucleophiles Atifah Najib, Koji Hirano,* and Masahiro Miura* Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka , Japan Contents Instrumentation and Chemicals Experimental Procedures Detailed Optimization Studies X-Ray Analysis Chiral HPLC Charts of Enantioenriched Products Characterization Data for Products S1 S2 S3 S4 S5 S6 S7 S27 S28 S58 Instrumentation and Chemicals 1 H, 13 C, and 19 F NMR spectra were recorded at 400 MHz, 100 MHz, and 376 MHz, respectively, for CDCl 3 solutions. HRMS data were obtained by APCI using TOF. GC analysis was carried out using a silicon OV-17 column (2.6 mm i.d. x 1.5 m) or a CBP-1 capillary column (0.5 mm i.d. x 25 m). TLC analyses were performed on commercial glass plates bearing a 0.25 mm layer of Merck silica gel 60F 254. Silica gel (Wakosil C-200) was used for column chromatography. Gel permeation chromatography (GPC) was performed by LC-6AD (pump, SHIMADZU, 3.5 ml/min CHCl 3 ) and SPD-20A (UV detector, SHIMADZU, 254 nm) with two in-line GPC H-2001 (20 x 500 mm, particle size: 15 µm) and H-2002 columns (20 x 500 mm, particle size: 15 µm) (preparative columns, Shodex, CHCl 3 eluent) or by LC-20AR (pump, SHIMADZU, 7.5 ml/min EtOAc) and SPD-20A (UV detector, SHIMADZU, 254 nm) with two in-line YMC-GPC T2000 (20 x 600 mm, particle size: 10 µm) (preparative columns, YMC, EtOAc eluent). Unless otherwise noted, materials obtained from commercial suppliers were used as received. MeCN was dried on a Glass Contour Solvent dispensing system (Nikko Hansen & Co., Ltd.) prior to use. DMSO was freshly distilled from CaH 2. (R)- and (S)-BINAP were purchased from Aldrich. [CpPd(h 3 -C 3 H 5 )] was prepared S1
2 according to the literature. 1 Starting carbonates 1, including (S)-1a, were synthesized from the corresponding carbinols. 2 All reactions were carried out under nitrogen atmosphere unless otherwise noted. 1 Tatsuno, Y.; Yoshida, T.; Otsuka, S.; Al-Salem, N.; Shaw, B. L. Inorg. Synth. 1990, 28, (a) Braga, A. L.; Paixão, M. W.; Westermann, B.; Schneider, P. H.; Wessjohann, L. A. J. Org. Chem. 2008, 73, (b) Tabuchi, S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2014, 79, (c) Tabuchi, S.; Hirano, K.; Miura, M. Chem. Eur. J. 2015, 21, S2
3 Experimental Procedures Synthesis of (R)-3aa (0.25 mmol scale; Table 1, entry 1): In a glovebox filled with nitrogen (R)-BINAP (7.8 mg, mmol), K 2 CO 3 (69.1 mg, 0.5 mmol), and CpPd(h 3 -C 3 H 5 ) (2.7 mg, mmol) were placed in a 20 ml two neck flask. The flask was sealed with a septum and taken out of the glovebox. MeCN (2.0 ml) was added, and the suspension was stirred for 10 min. A solution of tert-butyl (2-naphthyl (phenyl) methyl) carbonate (1a; 83.6 mg, 0.25 mmol) and N-methyl-N-tosylamide (2a; 55.6 mg, 0.30 mmol) in MeCN (1.0 ml) was then added to the flask, and the suspension was stirred for 6 h at 60 C. The resulting mixture was quenched with water and then extracted three times with ethyl acetate. The combined organic layer was dried over sodium sulfate. Concentration in vacuo and subsequent purification by column chromatography on silica gel with hexane/ethyl acetate (1/10 to 1/5 v/v) as an eluent gave (R)-N,4-dimethyl-N-(naphthalen-2-yl(phenyl)methyl)benzenesulfonamide [(R)-3aa; 79.3 mg, 0.20 mmol, 92:8 er] in 80% yield: enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic sample (Chiralcel OD-H column, 95/5 hexane/2-propanol, 0.50 ml/min, major isomer: t R = 24.7 min, minor isomer: t R = 29.2 min). Synthesis of (R)-3ia (1.0 mmol scale; Scheme 3): In a glovebox filled with nitrogen (R)-BINAP (31.1 mg, 0.05 mmol), K 2 CO 3 (276.4 mg, 2.0 mmol), tert-butyl (phenanthren-9-yl (phenyl) methyl) carbonate (384.5 mg, 1.0 mmol), and CpPd(h 3 -C 3 H 5 ) (10.6 mg, 0.05 mmol) were placed in a 50 ml two neck flask. The flask was sealed with a septum and taken out of the glovebox. MeCN (10 ml) was added, and the suspension was stirred for 10 min. A solution of N-methyl-N-tosylamide (2a; 22.3 mg, 1.20 mmol) in MeCN (2.0 ml) was then added to the flask, and the suspension was stirred for 6 h at 60 C. The resulting mixture was quenched with water and then extracted three times with ethyl acetate. The combined organic layer was dried over sodium sulfate. Concentration in vacuo and subsequent purification by column chromatography on silica gel with hexane/ethyl acetate (1/5 v/v) as an eluent gave (R)-N,4-dimethyl-N-(phenanthren-9-yl(phenyl)methyl)benzenesulfonamide [(R)-3ia; mg, 0.92 mmol, 98:2 er] in 92% yield: enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic sample (Chiralpak AD-H column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 27.5 min, minor isomer: t R = 30.6 min). S3
4 Detailed Optimization Studies Table S1. Optimization Studies [a] 1a OBoc + Ts N H Me 2a (1.2 equiv) [CpPd(η 3 -C 3 H 5 )] (5 mol %) chiral ligand (5 mol %) base (2.0 equiv) solvent, conditions Ts Me N 3aa entry chiral ligand base solvent conditions yield (%), [b] er [c] 1 (S,S)-BDPP none MeCN 80 C, 3 h 46, 66:34 2 (R,R)-DPPBA none MeCN 80 C, 3 h 0, n.d. 3 (R)-BINAP none MeCN 80 C, 3 h 77, 86:14 4 (R)-Xyl-BINAP none MeCN 80 C, 3 h 74, 74:26 5 (R)-DTBM-BINAP none MeCN 80 C, 3 h 60, 72:28 6 (R)-H 8 -BINAP none MeCN 80 C, 3 h 70, 87:13 7 (R)-SEGPHOS none MeCN 80 C, 3 h trace, n.d. 8 (R)-DM-SEGPHOS none MeCN 80 C, 3 h trace, n.d. 9 (R)-DTBM-SEGPHOS none MeCN 80 C, 3 h 48, 84:16 10 (R)-MeO-BIPHEP none MeCN 80 C, 3 h 61, 79:21 11 (R)-DTBM-MeO-BIPHEP none MeCN 80 C, 3 h 68, 56:44 12 (R)-BINAP none MeCN 60 C, 6 h 45, 94:6 13 (R)-BINAP Na 2 CO 3 MeCN 60 C, 6 h 59, 91:9 14 (R)-BINAP K 2 CO 3 MeCN 60 C, 6 h 79, 92:8 15 (R)-BINAP Cs 2 CO 3 MeCN 60 C, 6 h 65, 90:10 16 (R)-BINAP NaOAc MeCN 60 C, 6 h 50, 90:10 17 (R)-BINAP KOAc MeCN 60 C, 6 h 34, 92:8 18 (R)-BINAP Et 3 N MeCN 60 C, 6 h 39, 93:7 19 (R)-BINAP i-pr 2 NEt MeCN 60 C, 6 h 5 (NMR), n.d. 20 (R)-BINAP K 2 CO 3 DMSO 60 C, 6 h 34, 83:17 21 (R)-BINAP none DMSO 80 C, 3 h 37, 87:13 22 (R)-H 8 -BINAP K 2 CO 3 MeCN 60 C, 6 h 17, 93:7 23 (R)-BINAP K 2 CO 3 MeCN 50 C, 24 h 52, 80:20 [a] Reaction conditions: [CpPd(h 3 -C 3 H 5 )] (0.013 mmol), ligand (0.013 mmol), base (0.50 mmol), 1a (0.25 mmol), 2a (0.30 mmol), MeCN (3.0 ml), N 2. [b] Isolated yields are shown. [c] The enantiomeric ratios (er) are determined by HPLC analysis on a chiral stationary phase. n.d. = not S4
5 determined. O O NH HN Ph 2 P PPh 2 PPh (S,S)-BDPP 2 Ph 2 P (R,R)-DPPBA PAr 2 PAr 2 Ar = Ph: (R)-BINAP Ar = 3,5-Me 2 C 6 H 3 : (R)-Xyl-BINAP Ar = 3,5-(t-Bu) 2-4-MeOC 6 H 2 : (R)-DTBM-BINAP O MeO MeO PAr 2 PAr 2 O O PAr 2 PAr 2 PPh 2 PPh 2 Ar = Ph: (R)-MeO-BIPHEP Ar = 3,5-(t-Bu) 2-4-MeOC 6 H 2 : (R)-DTBM-MeO-BIPHEP O Ar = Ph: (R)-SEGPHOS Ar = 3,5-Me 2 C 6 H 3 : (R)-DM-SEGPHOS Ar = 3,5-(t-Bu) 2-4-MeOC 6 H 2 : (R)-DTBM-SEGPHOS (R)-H 8 -BINAP S5
6 X-Ray Analysis The X-ray quality crystals of (R)-3aa were grown from heptane/ethyl acetate. Ts N Me (R)-3aa, 92:8 er [α] D (c 0.50, CHCl 3 ) Figure S1. ORTEP Drawing (CCDC ) and Specific Rotation of (R)-3aa S6
7 Chiral HPLC Charts of Enantioenriched Products 3aa: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALCEL OD-H column, 95/5 n-hexane/2-propanol, 0.50 ml/min, major isomer: t R = 24.7 min, minor isomer: t R = 29.2 min, UV detection at 250 nm, 30 o C). rac-3aa (R)-3aa S7
8 3ab: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALCEL OD-H column, 95/5 n-hexane/2-propanol, 0.50 ml/min, major isomer: t R = 27.7 min, minor isomer: t R = 36.8 min, UV detection at 220 nm, 30 o C). rac-3ab (R)-3ab S8
9 3ac: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALCEL OD-H column, 95/5 n-hexane/2-propanol, 0.50 ml/min, major isomer: t R = 25.4 min, minor isomer: t R = 28.1 min, UV detection at 250 nm, 30 o C). rac-3ac (R)-3ac S9
10 3ad: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALCEL OD-H column, 95/5 n-hexane/2-propanol, 0.50 ml/min, major isomer: t R = 15.8 min, minor isomer: t R = 20.3 min, UV detection at 250 nm, 30 o C). rac-3ad (R)-3ad S10
11 3ae: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALCEL OD-H column, 97/3 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 19.1 min, minor isomer: t R = 20.5 min, UV detection at 210 nm, 30 o C). rac-3ae (R)-3ae S11
12 3af: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALCEL OD-H column, 97/3 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 23.8 min, minor isomer: t R = 26.9 min, UV detection at 270 nm, 30 o C). rac-3af (R)-3af S12
13 The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 95/5 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 8.7 min, minor isomer: t R = 12.3 min, UV detection at 260 nm, 30 o C). rac-3ag (R)-3ag S13
14 3ba: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 99.5/0.5 n-hexane/2-propanol, 2.5 ml/min (60 min) then 90/10 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 79.7 min, minor isomer: t R = 85.4 min, UV detection at 228 nm, 30 o C). rac-3ba (R)-3ba S14
15 3ca: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 95/5 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 21.8 min, minor isomer: t R = 23.2 min, UV detection at 220 nm, 30 o C). rac-3ca (R)-3ca S15
16 3da: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 95/5 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 35.7 min, minor isomer: t R = 37.9 min, UV detection at 230 nm, 30 o C). rac-3da (R)-3da S16
17 3ea: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 97/3 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 47.9 min, minor isomer: t R = 44.1 min, UV detection at nm, 30 o C). rac-3ea (S)-3ea S17
18 3fa: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 97/3 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 20.5 min, minor isomer: t R = 18.7 min, UV detection at 220 nm, 30 o C). rac-3fa (S)-3fa S18
19 3ga: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALCEL OD-H column, 95/5 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 15.8 min, minor isomer: t R = 18.3 min, UV detection at 235 nm, 30 o C). rac-3ga (R)-3ga S19
20 3ge: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 95/5 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 32.5 min, minor isomer: t R = 36.7 min, UV detection at 235 nm, 30 o C). rac-3ge (R)-3ge S20
21 3ha: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 95/5 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 24.7 min, minor isomer: t R = 19.4 min, UV detection at 220 nm, 30 o C). rac-3ha (R)-3ha S21
22 3ia: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 95/5 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = min, minor isomer: t R = 29.2 min, UV detection at 260 nm, 30 o C). rac-3ia (R)-3ia S22
23 3ja: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 95/5 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 24.0 min, minor isomer: t R = 20.3 min, UV detection at 220 nm, 30 o C). rac-3ja (R)-3ja S23
24 3ka: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 95/5 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 25.0 min, minor isomer: t R = 29.4 min, UV detection at 230 nm, 30 o C). rac-3ka (R)-3ka S24
25 6aa: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 95/5 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 7.1 min, minor isomer: t R = 7.7 min, UV detection at 235 nm, 30 o C). rac-6aa (R)-6aa S25
26 6ab: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 95/5 n-hexane/2-propanol, 1.00 ml/min, major isomer: t R = 5.5 min, minor isomer: t R = 6.2 min, UV detection at 235 nm, 30 o C). rac-6ab (R)- 6ab S26
27 6ac: The enantiomeric ratio was determined by HPLC analysis in comparison with authentic racemic material (CHIRALPAK AD-H column, 95/5 n-hexane/2-propanol, 1.0 ml/min, major isomer: t R = 9.0 min, minor isomer: t R = 10.2 min, UV detection at 235 nm, 30 o C). rac-6ac (R)-6ac S27
28 Characterization Data for Products 1 H, 13 C{ 1 H}, and 19 F NMR spectra for all compounds are attached in the last part. N,4-Dimethyl-N-(naphthalen-2-yl(phenyl)methyl)benzenesulfonamide (3aa) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/10 to 1/5 v/v) as an eluent; 79.3 mg (79%, 92:8 er); white solid; mp C; 1 H NMR (400 MHz, CDCl 3 ) δ 2.38 (s, 3H), 2.74 (s, 3H), 6.61 (s, 1H), (m, 2H), (m, 3H), (m, 3H), 7.43 (s, 1H), (m, 2H), (m, 3H), 7.73 (d, J = 8.6 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 21.49, 31.36, 64.36, , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 25 H 22 NO 2 S: , found: Chiralcel OD-H column, 95/5 hexane/2-propanol, 0.50 ml/min, major isomer: t R = 24.7 min, minor isomer: t R = 29.2 min. 4-Methoxy-N-methyl-N-(naphthalen-2-yl(phenyl)methyl)benzenesulfonamide (3ab) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/5 v/v) as an eluent; 49.1 mg (47%, 90:10 er); white solid; mp C; 1 H NMR (400 MHz, CDCl 3 ) δ 2.73 (s, 3H), 3.81 (s, 3H), 6.61 (s, 1H), 6.84 (d, J = 9.0 Hz, 2H), (m, 2H), 7.20 (dd, J = 8.6, 1.8 Hz,1H), (m, 3H), (m, 3H), (m, 3H), 7.74 (d, J = 8.6 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 31.34, 55.57, 64.34, (two peaks overlapped), , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + for C 25 H 22 NO 3 S: , found: Chiralcel OD-H column, 95/5 hexane/2-propanol, 0.50 ml/min, major isomer: t R = 27.7 min, minor isomer: t R = 36.8 min. 4-Chloro-N-methyl-N-(naphthalen-2-yl(phenyl)methyl)benzenesulfonamide (3ac) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/10 to 1/5 v/v) as an eluent; 59.1 mg (56%, 90:10 er); oil; 1 H NMR (400 MHz, CDCl 3 ) δ 2.76 (s, 3H), 6.61 (s, 1H), (m, 2H), 7.21 (dd, J = 8.6, 1.8 Hz, 1H), (m, 5H), 7.43 (s, 1H), (m, 2H), (m, 3H), 7.76 (d, J = 8.6 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 27.90, 64.60, , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 24 H 19 ClNO 2 S: , found: Chiralcel OD-H column, 95/5 hexane/2-propanol, 0.50 ml/min, major isomer: t R = 25.4 min, minor isomer: t R = 28.1 min. S28
29 N,2,4,6-Tetramethyl-N-(naphthalen-2-yl(phenyl)methyl)benzenesulfonamide (3ad) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/80 v/v) as an eluent; 76.2 mg (71%, 91:9 er); white solid; mp C; 1 H NMR (400 MHz, CDCl 3 ) δ 2.30 (s, 3H), 2.54 (s, 6H), 2.74 (s, 3H), 6.49 (s, 1H), 6.92 (s, 2H), (m, 2H), (m, 4H), (m, 3H), (m, 1H), 7.77 (d, J = 8.6 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 27.93, 31.34, 55.58, 64.32, , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 27 H 26 NO 2 S: , found: Chiralcel OD-H column, 95/5 hexane/2-propanol, 0.50 ml/min, major isomer: t R = 15.8 min, minor isomer: t R = 20.3 min. N-Methyl-N-(naphthalen-2-yl(phenyl)methyl)thiophene-2-sulfonamide (3ae) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/10 to 1/5 v/v) as an eluent; 78.0 mg (79%, 93:7 er); oil; 1 H NMR (400 MHz, CDCl 3 ) δ 2.80 (s, 3H), 6.62 (s, 1H), 7.00 (dd, J = 3.8, 5.0 Hz, 1H), (m, 2H), 7.20 (dd, J = 8.6 Hz, 1.8 Hz, 1H), (m, 3H), (m, 5H), (m, 1H), 7.75 (d, J = 8.7 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 31.54, 64.80, , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 22 H 18 NO 2 S 2 : , found: Chiralcel OD-H column, 97/3 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 19.1 min, minor isomer: t R = 20.5 min. N-Methyl-N-(naphthalen-2-yl(phenyl)methyl)methanesulfonamide (3af) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/5 v/v) as an eluent; 41.6 mg (51%, 90:10 er); brown solid; mp C; 1 H NMR (400 MHz, CDCl 3 ) δ 2.68 (s, 3H), 2.83 (s, 3H), 6.57 (s, 1H), (m, 6H), (m, 2H), 7.71 (s, 1H), (m, 1H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 30.92, 38.29, 64.53, , (two peaks overlapped), , , (two peaks overlapped), , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 19 H 18 NO 2 S: , found: Chiralcel OD-H column, 97/3 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 23.8 min, minor isomer: t R = 26.9 min. 4-(Naphthalen-2-yl(phenyl)methyl)morpholine (3ag) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/20 to 1/10 v/v) as an eluent; 44.7 mg (59%, 88:12 er); white solid; mp S29
30 C; 1 H NMR (400 MHz, CDCl 3 ) δ 2.44 (d, J = 4.6 Hz, 4H), 3.73 (t, J = 4.6 Hz, 4H), 4.37 (s, 1H), 7.17 (tt, J = 7.3, 1.3 Hz, 1H), (m, 2H), 7.42 (dtd, J = 14.6, 6.9, 1.4 Hz, 2H), (m, 2H), 7.60 (dd, J = 8.6, 1.6 Hz, 1H), (m, 3H), 7.84 (s, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 52.78, 67.23, 76.83, , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 21 H 20 NO: , found: Chiralpak AD-H column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 8.7 min, minor isomer: t R = 12.3 min. N-((4-Methoxyphenyl)(naphthalen-2-yl)methyl)-N,4-dimethylbenzenesulfonamide (3ba) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/5 v/v) as an eluent; 86.3 mg (80%, 89:11 er); oil; 1 H NMR (400 MHz, CDCl 3 ) δ 2.38 (s, 3H), 2.73 (s, 3H), 3.80 (s, 3H), 6.56 (s, 1H), 6.80 (d, J = 8.8 Hz, 2H), 7.02 (d, J = 8.4 Hz, 2H), (m, 3H), (m, 3H), (m, 3H), 7.73 (d, J = 8.6 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 21.47, 31.22, 55.30, 63.86, , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 26 H 24 NO 3 S: , found: Chiralpak AD-H column, 99.5/0.5 hexane/2-propanol, 2.5 ml/min (60 min) then 90/10 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 79.7 min, minor isomer: t R = 85.4 min. N,4-Dimethyl-N-(naphthalen-2-yl(4-trifluoromethyl)phenyl)methyl)benzenesulfonamide (3ca) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/5 v/v) as an eluent; 63.4 mg (54%, 84:16 er); white solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ) δ 2.40 (s, 3H), 2.74 (s, 3H), 6.64 (s, 1H), 7.12 (dd, J = 8.7, 1.9 Hz, 1H), 7.21 (d, J = 8.0 Hz, 2H), 7.29 (d, J = 8.0 Hz, 2H), 7.35 (s, 1H), (m, 2H), 7.56 (d, J = 8.2 Hz, 2H), (m, 3H), 7.75 (d, J = 8.6 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 21.49, 31.43, 64.00, (q, J = 271 Hz), (q, J = 3.4 Hz), , 126.8, , , , , , , , , (q, J = 31.8 Hz), , , , , , ; 19 F NMR (376 MHz, CDCl 3 ) δ ; HRMS (APCI) m/z (M-H) + Calcd for C 26 H 21 F 3 NO 2 S: , found: Chiralpak AD-H column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 21.8 min, minor isomer: t R = 23.2 min. N-((4-Chlorophenyl)(naphthalen-2-yl)methyl)-N,4-dimethylbenzenesulfonamide (3da) Purified S30
31 by column chromatography on silica gel with ethyl acetate/hexane (1/10 to 1/5 v/v) as an eluent; 67.4 mg (63%, 87:13 er); oil; 1 H NMR (400 MHz, CDCl 3 ) δ 2.39 (s, 3H), 2.72 (s, 3H), 6.57 (s, 1H), 7.08 (d, J = 8.3 Hz, 2H), 7.14 (dd, J = 8.6, 1.8 Hz, 1H), 7.21 (d, J = 8.0 Hz, 2H), (m, 2H), 7.38 (s, 1H), (m, 2H), (m, 3H), 7.74 (d, J = 8.5 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 21.52, 31.30, 63.74, , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 25 H 21 ClNO 2 S: , found: Chiralpak AD-H column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 35.7 min, minor isomer: t R = 37.9 min, UV detection at 230 nm, 30 o C). N-((3-Methoxyphenyl)(naphthalen-2-yl)methyl)-N,4-dimethylbenzenesulfonamide (3ea) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/5 v/v) as an eluent; 89.7 mg (83%, 92:8 er); white solid; mp C; 1 H NMR (400 MHz, CDCl 3 ) δ 2.38 (s, 3H), 2.75 (s, 3H), 3.69 (s, 3H), 6.57 (s, 1H), 6.63 (s, 1H), 6.69 (dt, J = 7.6, 0.8 Hz, 1H), 6.82 (dd, J = 8.1, 2.4 Hz, 1H), (m, 4H), (m, 3H), (m, 3H), 7.73 (d, J = 8.6 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 21.49, 31.46, 55.17, 64.30, , , , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 26 H 24 NO 3 S: , found: Chiralpak AD-H column, 97/3 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 47.9 min, minor isomer: t R = 44.1 min. N,4-Dimethyl-N-(naphthalen-2-yl(o-tolyl)methyl)benzenesulfonamide (3fa) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/10 to 1/5 v/v) as an eluent; 74.1 mg (71%, 96:4 er); oil; 1 H NMR (400 MHz, CDCl 3 ) δ 2.28 (s, 3H), 2.36 (s, 3H), 2.72 (s, 3H), 6.73 (s, 1H), (d, J = 7.6 Hz, 1H), (m, 4H), 7.16 (s, 1H), (m, 2H), (m, 2H), 7.50 (dd, J = 7.2, 1.7 Hz, 1H), 7.55 (dd, J = 6.6, 1.8 Hz, 2H), 7.69 (d, J = 8.6 Hz, 1H), 7.78 (dd, J = 7.3, 1.6 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 19.78, 21.47, 32.30, 62.01, , , , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 26 H 24 NO 2 S: , found: Chiralpak AD-H column, 97/3 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 20.5 min, minor isomer: t R = 18.7 min. S31
32 N-((6-Methoxynaphthalen-2-yl)(phenyl)methyl)-N,4-dimethylbenzenesulfonamide (3ga) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/10 to 1/5 v/v) as an eluent; 68.2 mg (63%, 89:11 er); oil; 1 H NMR (400 MHz, CDCl 3 ) δ 2.37 (s, 3H), 2.72 (s, 3H), 3.90 (s, 3H), 6.58 (s, 1H), (m, 7H), (m, 3H), 7.33 (s, 1H), 7.52 (d, J = 8.6 Hz, 1H), 7.63 (d, J = 8.2 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 21.50, 31.30, 55.36, 64.29, , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 26 H 24 NO 3 S: , found: Chiralcel OD-H column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 15.8 min, minor isomer: t R = 18.3 min. N-((6-Methoxynaphthalen-2-yl)(phenyl)methyl)-N-methylthiophene-2-sulfonamide (3ge) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/10 to 1/5 v/v) as an eluent; 67.5 mg (62%, 92:8 er); oil; 1 H NMR (400 MHz, CDCl 3 ) δ 2.79 (s, 3H), 3.91 (s, 3H), 6.58 (s, 1H), 6.99 (dd, J = 3.8, 5.0 Hz, 1H), (m, 5H), (m, 3H), 7.40 (s, 1H), (m, 2H), 7.58 (d, J = 8.8 Hz, 1H), 7.64 (d, J = 8.6 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 31.47, 55.35, 64.75, , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 23 H 20 NO 3 S 2 : , found: Chiralpak AD-H column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 32.5 min, minor isomer: t R = 36.7 min. N,4-Dimethyl-N-(naphthalen-1-yl(phenyl)methyl)benzenesulfonamide (3ha) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/10 to 1/5 v/v) as an eluent; 62.6 mg (62%, 82:18 er); white solid; mp C; 1 H NMR (400 MHz, CDCl 3 ) δ 2.38 (s, 3H), 2.69 (s, 3H), 6.96 (d, J = 6.8 Hz, 2H), (m, 7H), 7.32 (t, J = 7.8 Hz, 1H), (m, 2H), 7.55 (d, J = 8.2 Hz, 2H), 7.78 (d, J = 8.2 Hz, 1H), 7.85 (d, J = 7.5 Hz, 1H), 8.02 (d, J = 8.0 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 21.51, 32.30, 61.70, , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 25 H 22 NO 2 S: , found: Chiralpak AD-H column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 24.7 min, minor isomer: t R = 19.4 min N,4-Dimethyl-N-(phenanthren-9-yl(phenyl)methyl)benzenesulfonamide (3ia) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/5 v/v) as an eluent; mg (>99%, 96:4 S32
33 er); white solid; mp C; 1 H NMR (400 MHz, CDCl 3 ) δ 2.34 (s, 3H), 2.76 (s, 3H), (m, 2H), 7.11 (d, J = 8.0 Hz, 2H), 7.15 (s, 1H), (m, 3H), 7.31 (s, 1H), (m, 7H), 8.00 (d, J = 8.3 Hz, 1H), 8.65 (d, J = 8.2 Hz, 1H), 8.71 (d, J = 7.8 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 21.46, 32.38, 62.18, , , , , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 29 H 24 NO 2 S: , found: Chiralpak AD-H column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 25.9 min, minor isomer: t R = 29.2 min. N,4-Dimethyl-N-(1-(naphthalen-2-yl)ethyl)benzenesulfonamide (3ja) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/10 to 1/5 v/v) as an eluent; 40.0 mg (47%, 52:48 er); white solid; mp C; 1 H NMR (400 MHz, CDCl 3 ) δ 1.39 (d, J = 7.0 Hz, 3H), 2.44 (s, 3H), 2.58 (s, 3H), 5.43 (q, J = 7.0 Hz, 1H), 7.32 (d, J = 8.0 Hz, 2H), (m, 3H), 7.64 (s, 1H), (m, 5H); 13 C NMR (100 MHz, CDCl 3 ) 15.04, 21.57, 38.46, 54.90, , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 20 H 20 NO 2 S: , found: Chiralpak AD-H column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 24.0 min, minor isomer: t R = 20.3 min. N-(Benzo[b]thiophen-2-yl(phenyl)methyl)-N,4-dimethylbenzenesulfonamide (3ka) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/10 v/v) as an eluent followed by GPC with ethyl acetate; 34.9 mg (34%, 88:12 er); white solid; mp C; 1 H NMR (400 MHz, CDCl 3 ) δ 2.36 (s, 3H), 2.79 (s, 3H), 6.71 (s, 1H), 6.94 (s, 1H), 7.17 (d, J = 8.0 Hz, 2H), (m, 7H), (m, 3H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 21.50, 31.04, 61.04, , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 23 H 20 NO 2 S 2 : , found: Chiralpak AD-H column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 25.0 min, minor isomer: t R = 29.4 min. N-(2-Benzylbenzo[b]thiophen-3-yl)-N,4-dimethylbenzenesulfonamide (3ka ) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/10 v/v) as an eluent followed by GPC with ethyl acetate; 21.7 mg (21%); oil; 1 H NMR (400 MHz, CDCl 3 ) δ 2.44 (s, 3H), 3.22 (s, 3H), 4.18 (d, J = 16 Hz, 1H), 4.31 (d, J = 16 Hz, 1H), 6.80 (d, J = 8.0 Hz, 1H), 7.60 (ddd, J = 8.1, 7.2, 1.0 Hz, 1H), 7.20 S33
34 (ddd, J = 8.1, 7.2, 1.0 Hz, 1H), (m, 7H), 7.66 (t, J = 8.1 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 21.59, 34.19, 37.72, , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M+H) + Calcd for C 23 H 22 NO 2 S 2 : , found: (Phenoxy(phenyl)methyl)naphthalene (6aa) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/10 to 1/5 v/v) as an eluent; 64.1 mg (83%, 86:14 er); white solid; mp C; 1 H NMR (400 MHz, CDCl 3 ) δ 6.36 (s, 1H), 6.89 (tt, J = 7.3, 1.0 Hz, 1H), (m, 2H), (m, 3H), (m, 2H), (m, 4H), 7.52 (dd, J = 8.6, 1.7 Hz, 1H), (m, 3H), 7.87 (s, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 81.96, , , , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 23 H 17 O: , found: Chiralpak AD-H column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 7.1 min, minor isomer: t R = 7.7 min. 2-((4-(tert-Butyl)phenoxy)(phenyl)methyl)naphthalene (6ab) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/150 v/v) as an eluent followed by GPC with chloroform; 67.8 mg (74%, 88:12 er); white solid; mp C; 1 H NMR (400 MHz, CDCl 3 ) δ 1.24 (s, 9H), 6.33 (s, 1H), (m, 2H), (m, 3H), (m, 2H), (m, 4H), 7.52 (dd, J = 8.6, 1.6 Hz, 1H), (m, 3H), 7.87 (s, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 31.54, 34.11, 81.97, , , , , (two peaks overlapped), , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 27 H 25 O: , found: Chiralpak AD-H column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 5.5 min, minor isomer: t R = 6.2 min. 2-(Naphthalen-2-yl(phenyl)methoxy)naphthalene (6ac) Purified by column chromatography on silica gel with ethyl acetate/hexane (1/150 v/v) as an eluent followed by GPC with chloroform; 74.8 mg (83%, 91:9 er); white solid; mp C; 1 H NMR (400 MHz, CDCl 3 ) δ 6.53 (s, 1H), 7.18 (d, J = 2.4 Hz, 1H), (m, 3H), (m, 3H), (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 3H), 7.94 (s, 1H); 13 C NMR (100 MHz, CDCl 3 ) 81.35, , , , , , , (two peaks overlapped), , , , , , , , , , , , , , , , ; HRMS (APCI) m/z (M-H) + Calcd for C 27 H 19 O: , found: Chiralpak AD-H S34
35 column, 95/5 hexane/2-propanol, 1.0 ml/min, major isomer: t R = 9.0 min, minor isomer: t R = 10.2 min. S35
36 [ 1 H and 13 C NMR Spectra of 3aa] Ts N Me 3aa S36
37 [ 1 H and 13 C NMR Spectra of 3ab] MeO O O S N Me 3ab S37
38 [ 1 H and 13 C NMR Spectra of 3ac] Cl O O S N Me 3ac S38
39 [ 1 H and 13 C NMR Spectra of 3ad] O O S N Me 3ad S39
40 [ 1 H and 13 C NMR Spectra of 3ae] S O O S N Me 3ae S40
41 [ 1 H and 13 C NMR Spectra of 3af] O O S Me N Me 3af S41
42 [ 1 H and 13 C NMR Spectra of 3ag] O N 3ag S42
43 [ 1 H and 13 C NMR Spectra of 3ba] Ts N Me 3ba OMe S43
44 [ 1 H, 13 C, and 19 F NMR Spectra of 3ca] Ts N Me 3ca CF 3 S44
45 S45
46 [ 1 H and 13 C NMR Spectra of 3da] Ts N Me 3da Cl S46
47 [ 1 H and 13 C NMR Spectra of 3ea] Ts N Me 3ea OMe S47
48 [ 1 H and 13 C NMR Spectra of 3fa] Ts N Me Me 3fa S48
49 [ 1 H and 13 C NMR Spectra of 3ga] Ts N Me MeO 3ga S49
50 [ 1 H and 13 C NMR Spectra of 3ge] S O O S N Me MeO 3ge S50
51 [ 1 H and 13 C NMR Spectra of 3ha] Ts N Me 3ha S51
52 [ 1 H and 13 C NMR Spectra of 3ia] Ts N Me 3ia S52
53 [ 1 H and 13 C NMR Spectra of 3ja] Ts N Me 3ja S53
54 [ 1 H and 13 C NMR Spectra of 3ka] Ts N Me S 3ka S54
55 [ 1 H and 13 C NMR Spectra of 3ka ] Ts Me N S 3ka' S55
56 [ 1 H and 13 C NMR Spectra of 6aa] O 6aa S56
57 [ 1 H and 13 C NMR Spectra of 6ab] t-bu O 6ab S57
58 [ 1 H, 13 C, and 19 F NMR Spectra of 6ac] O 6ac S58
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