Supporting Information For: Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes
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- Αελλαι Μιχαλολιάκος
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1 Supporting Information For: Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes Xiao-Hui Yang and Vy M. Dong* Department of Chemistry, University of California, Irvine, California , United States Table of Contents 1. General...S1 2. Typical procedures for the hydrofunctionalization of 1,3-dienes...S2 3. Typical procedures for the hydroamination of 1,3-dienes...S3 4. Synthesis of N-allylic indole 5...S9 5. References...S10 6. NMR spectra...s SFC spectra...s General: Commercial reagents were purchased from Sigma Aldrich, Strem, Alfa Aesar, Acros Organics or TCI and used without further purification. 1,2-Dichloroethane and tetrahydrofuran were purified using an Innovative Technologies Pure Solv system, degassed by three freeze-pump-thaw cycles, and stored over 3A MS within a N 2 filled glove box. All experiments were performed in oven-dried or flame-dried glassware. Reactions were monitored using either thin-layer chromatography (TLC) or gas chromatography using an Agilent Technologies 7890A GC system equipped with an Agilent Technologies 5975C inert XL EI/CI MSD. Visualization of the developed plates was performed under UV light (254 nm) or KMnO 4 stain. Organic solutions were concentrated under reduced pressure on a Büchi rotary evaporator. Column chromatography was performed with Silicycle Silia-P Flash Silica Gel using glass columns. Solvents were purchased from Fisher. 1 H and 13 C NMR spectra were recorded on Bruker CRYO500 or DRX400 spectrometer. 1 H NMR spectra were internally referenced to the residual solvent signal or TMS. 13 C NMR spectra were internally referenced to the residual solvent signal. Data for 1 H NMR are reported as follows: chemical shift (δ ppm), multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet), coupling constant (Hz), integration. Data for 13 C NMR are reported in terms of chemical shift (δ ppm). Infrared (IR) spectra were obtained on a Nicolet is5 FT-IR spectrometer with an id5 ATR, and are reported in terms of frequency of absorption (cm -1 ). High resolution mass spectra (HRMS) were obtained on a micromass 70S-250 spectrometer (EI) or an ABI/Sciex QStar Mass Spectrometer (ESI). Enantiomeric excesses for enantioselective reactions were determined by chiral SFC analysis using an Agilent Technologies HPLC (1200 series) system and Aurora A5 Fusion. 1,3-Dienes used here were known compounds and synthesized according to the reported methods. 1 S1
2 2. Typical procedures for the hydrofunctionalization of 1,3-dienes A mixture of [Rh(COD)Cl] 2 (2.0 mg, mmol), ligand (0.008 mmol), acid (0.1 mmol), nucleophile (0.20 mmol), 1,3-diene (0.30 mmol), and DCE (0.4 ml) were added to a 1 dram vial in the glove box. After heating the reaction mixture for 24 h, the resulting solution was cooled to rt. The selectivity was determined by 1 H NMR analysis of the reaction prior to purification. The product was purified by column chromatography on silica gel using hexanes/etoac (15:1). (E)-2-(4-(4-methoxyphenyl)but-3-en-2-yl)-1,3-diphenylpropane-1,3-dione Colorless oil, 51% yield 1 H NMR (500 MHz, CDCl 3) δ (m, 2H), (m, 2H), (m, 2H), (m, 4H), (m, 2H), (m, 2H), 6.31 (d, J = 16.0 Hz, 1H), 5.97 (dd, J = 16.0, 8.5 Hz, 1H), 5.31 (d, J = 9.0 Hz, 1H), 3.76 (s, 3H), (m, 1H), 1.21 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , , , , , 63.41, 55.39, 38.75, IR (ATR): 2961, 2835, 1694, 1510, 1447, 1246, 1175, 1030, 969, 688 cm -1. HRMS calculated for C 26H 25O 3 [M+H] , found (E)-1-methoxy-4-(3-(3-phenylpropoxy)but-1-en-1-yl)benzene Colorless oil, 37% yield. 1 H NMR (500 MHz, CDCl 3) δ (m, 2H), (m, 2H), (m, 3H), (m, 2H), 6.44 (d, J = 16.0 Hz, 1H), 5.98 (dd, J = 16.0, 7.5 Hz, 1H), (m, 1H), 3.81 (s, 3H), 3.52 (dt, J = 9.5, 6.5 Hz, 1H), 3.36 (dt, J = 9.5, 6.5 Hz, 1H), (m, 2H), (m, 2H), 1.33 (d, J = 6.5 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , 76.64, 67.35, 55.30, 32.40, 31.48, IR (ATR): 2930, 1607, 1509, 1453, 1245, 1174, 1033, 829, 744, 698 cm -1. HRMS calculated for C 20H 25O 2 [M+H] , found (E)-(4-(4-methoxyphenyl)but-3-en-2-yl)(4-tolyl)sulfane Colorless oil, 61% yield. 1 H NMR (500 MHz, CDCl 3) δ (m, 2H), (m, 2H), (m, 2H), (m, 2H), 6.16 (d, J = 16.0 Hz, 1H), 6.03 (dd, J = 16.0, 8.0 Hz, 1H), (m, 4H), 2.31 (s, 3H), 1.45 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , 55.42, 47.04, 21.26, IR (ATR): 2922, 1607, 1510, 1491, 1245, 1174, 1033, 962, 908, 807, 731 cm -1. HRMS calculated for C 18H 21OS [M+H] , found S2
3 3. Typical procedures for the hydroamination of 1,3-dienes A mixture of [Rh(COD)OMe] 2 (1.9 mg, mmol), JoSPOphos (4.0 mg, mmol), triphenylacetic acid (14.4 mg, 0.1 mmol), amine 1 (0.20 mmol), 1,3-diene 2 (0.30 mmol), and DCE (0.4 ml) were added to a 1 dram vial in the glove box. After heating the reaction mixture at 60 o C for 24 h, the resulting solution was cooled to rt. The selectivity was determined by 1 H NMR analysis of the reaction prior to purification. The product 3 was purified by column chromatography on silica gel using hexanes/etoac (15:1). (R, E)-4-chloro-1-(4-phenylbut-3-en-2-yl)indoline (3aa) 2 Colorless oil, 81% yield, 96% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (400 MHz, CD 2Cl 2) δ (m, 2H), (m, 2H), (m, 1H), (m, 2H), (m, 2H), 6.51 (d, J = 8.0 Hz, 1H), 6.33 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), (m, 2H), 2.94 (t, J = 8.4 Hz, 2H), 1.41 (d, J = 6.8 Hz, 3H). 13 C NMR (101 MHz, CDCl 3) δ , , , , , , , , , , , , 52.79, 47.65, 28.59, Chiral SFC: 250 mm CHIRALCEL IC, 3% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 3.5 min, t R2 (major) = 3.9 min. (R, E)-4-chloro-1-(4-phenylbut-3-en-2-yl)indoline (3ab) Colorless oil, 87% yield, 96% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 2H), (m, 2H), (m, 1H), (m, 1H), (m, 2H), 6.39 (d, J = 8.0 Hz, 1H), 6.29 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), (m, 2H), (m, 2H), 1.41 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , 53.03, 47.18, 27.85, IR (ATR): 2925, 2848, 1598, 1453, 1263, 1159, 966, 749 cm -1. HRMS calculated for C 18H 19ClN [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 4% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 5.2 min, t R2 (major) = 5.5 min. (R, E)-4-methyl-1-(4-phenylbut-3-en-2-yl)indoline (3ac) Colorless oil, 80% yield, 96% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 2H), (m, 2H), (m, 1H), 6.93 (t, J = 7.5 Hz, 1H), 6.57 (dd, J = 16.0, 1.0 Hz, 1H), 6.44 (d, J = 7.5 Hz, 1H), (m, 2H), (m, 1H), (m, 2H), (m, 2H), 2.18 (s, 3H), 1.40 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , 52.86, 47.36, 27.24, 18.65, IR (ATR): 2970, 2842, 1593, 1461, 1260, 1158, 967, 749, 735 cm -1. HRMS calculated for C 19H 22N [M+H] , found Chiral SFC: S3
4 250 mm CHIRALCEL IC, 10% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 3.1 min, t R2 (major) = 3.5 min. (R, E)-4-methoxy-1-(4-phenylbut-3-en-2-yl)indoline (3ad) Colorless oil, 80% yield, 97% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 2H), (m, 2H), (m, 1H), 7.00 (t, J = 8.0 Hz, 1H), 6.55 (dd, J = 16.0, 1.0 Hz, 1H), 6.32 (dd, J = 16.0, 6.0 Hz, 1H), (m, 2H), (m, 1H), 3.79 (s, 3H), (m, 2H), (m, 2H), 1.39 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , 55.51, 52.92, 47.74, 25.51, IR (ATR): 2970, 2835, 1612, 1464, 1255, 1160, 1086, 967, 749 cm -1. HRMS calculated for C 19H 22NO [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 10% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 4.2 min, t R2 (major) = 4.9 min. (R, E)-5-fluoro-1-(4-phenylbut-3-en-2-yl)indoline (3ae) Colorless oil, 82% yield, 99% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 2H), (m, 2H), (m 1H), (m, 1H), (m, 1H), 6.57 (dd, J = 16.0, 1.0 Hz, 1H), 6.42 (dd, J = 8.5, 4.5 Hz, 1H), 6.31 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), (m, 2H), 2.93 (t, J = 8.5 Hz, 2H), 1.40 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ (d, J = Hz), , , (d, J = 7.5 Hz), , , , , , (d, J = 22.5 Hz), (d, J = 23.8 Hz), (d, J = 8.8 Hz), 53.41, 48.22, (d, J = 2.5 Hz), IR (ATR): 2970, 2843, 1605, 1486, 1229, 1184, 966, 745 cm -1. HRMS calculated for C 18H 19FN [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 7% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 2.7 min, t R2 (major) = 3.0 min. (R, E)-5-chloro-1-(4-phenylbut-3-en-2-yl)indoline (3af) Colorless oil, 80% yield, 94% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (400 MHz, CD 2Cl 2) δ (m, 2H), (m, 2H), (m, 1H), (m, 2H), 6.56 (dd, J = 16.0, 1.2 Hz, 1H), 6.42 (d, J = 8.4 Hz, 1H), 6.28 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), (m, 2H), 2.93 (t, J = 8.4 Hz, 2H), 1.40 (d, J = 6.8 Hz, 3H). 13 C NMR (101 MHz, CDCl 3) δ , , , , , , , , , , , , 52.99, 47.87, 28.42, IR (ATR): 2969, 2841, 1601, 1586, 1254, 1179, 966, 751 cm -1. HRMS calculated for C 18H 19ClN [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 4% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 6.6 min, t R2 (major) = 7.2 min. (R, E)-5-bromo-1-(4-phenylbut-3-en-2-yl)indoline (3ag) S4
5 Colorless oil, 86% yield, 99% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CDCl 3) δ (m, 2H), (m, 2H), (m, 1H), (m, 2H), 6.56 (dd, J = 16.0, 1.5 Hz, 1H), (m, 1H), 6.28 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), (m, 2H), 2.95 (t, J = 8.5 Hz, 2H), 1.40 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , 52.92, 47.79, 28.36, IR (ATR): 2922, 2851, 1595, 1465, 1259, 1162, 966, 737, 751 cm -1. HRMS calculated for C 18H 19BrN [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 7% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 5.4 min, t R2 (major) = 6.0 min. (R, E)-5-methoxy-1-(4-phenylbut-3-en-2-yl)indoline (3ah) Colorless oil, 81% yield, 88% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 2H), (m, 2H), (m, 1H), (m, 1H), (m, 2H), 6.45 (d, J = 8.5 Hz, 1H), 6.33 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), 3.70 (s, 3H), (m, 2H), 2.90 (t, J = 8.5 Hz, 2H), 1.38 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , 56.21, 53.19, 48.23, 28.99, IR (ATR): 2932, 2828, 1593, 1488, 1234, 1139, 1034, 967, 745 cm -1. HRMS calculated for C 19H 22NO [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 5% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 5.8 min, t R2 (major) = 6.9 min. (R, E)-6-methyl-1-(4-phenylbut-3-en-2-yl)indoline (3ai) Colorless oil, 89% yield, 94% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 2H), (m, 2H), (m, 1H), 6.92 (d, J = 7.5 Hz, 1H), 6.57 (dd, J = 16.0, 1.0 Hz, 1H), (m, 1H), (m, 2H), (m, 1H), (m, 2H), 2.88 (t, J = 8.5 Hz, 2H), 2.26 (s, 3H), 1.40 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , 52.54, 47.73, 28.21, 21.86, IR (ATR): 2970, 2845, 1610, 1493, 1209, 1172, 1034, 967, 748 cm -1. HRMS calculated for C 19H 22N [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 5% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 3.2 min, t R2 (major) = 3.9 min. (R, E)-6-methoxy-1-(4-phenylbut-3-en-2-yl)indoline (3aj) Colorless oil, 88% yield, 98% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 2H), (m, 2H), (m, 1H), 6.91 (d, J = 8.0 Hz, 1H), 6.57 (d, J = 16.0 Hz, 1H), 6.32 (dd, J = 16.0, 6.0 Hz, 1H), (m, 2H), (m, 1H), 3.72 (s, 3H), (m, 2H), 2.87 (t, J = 8.5 Hz, 2H), 1.40 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , 95.51, 55.59, 52.68, 48.16, 27.73, IR (ATR): 2935, 2832, 1618, 1493, 1209, 1172, 1034, 967, 748 cm -1. HRMS calculated for C 19H 22NO [M+H] , found Chiral S5
6 SFC: 250 mm CHIRALCEL IC, 10% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 5.2 min, t R2 (major) = 7.3 min. (R, E)-1-(4-(4-fluorophenyl)but-3-en-2-yl)indoline (3ba) Colorless oil, 83% yield, 98% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 2H), (m, 4H), (m, 3H), 6.28 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), (m, 2H), 2.97 (t, J = 8.5 Hz, 2H), 1.43 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ (d, J = Hz), , (d, J = 3.8 Hz), , , , (d, J = 7.6 Hz), , , , (d, J = 21.3 Hz), , 52.74, 47.60, 28.56, IR (ATR): 2972, 2843, 1604, 1507, 1485, 1225, 1157, 969, 744, 713 cm -1. HRMS calculated for C 18H 19FN [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 7% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 3.1 min, t R2 (major) = 3.5 min. (R, E)-1-(4-(4-chlorophenyl)but-3-en-2-yl)indoline (3ca) Colorless oil, 82% yield, 94% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 4H), (m, 2H), (m, 3H), 6.31 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), (m, 2H), 2.94 (t, J = 8.5 Hz, 2H), 1.39 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , 52.71, 47.62, 28.55, IR (ATR): 2970, 2844, 1605, 1486, 1259, 1089, 1011, 968, 742, 713 cm -1. HRMS calculated for C 18H 19ClN [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 10% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 3.5 min, t R2 (major) = 3.9 min. (R, E)-1-(4-(4-bromophenyl)but-3-en-2-yl)indoline (3da) Colorless oil, 85% yield, 93% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (400 MHz, CD 2Cl 2) δ (m, 2H), (m, 2H), (m, 2H), (m 1H), (m, 2H), 6.33 (dd, J = 16.0, 5.6 Hz, 1H), (m, 1H), (m, 2H), 2.94 (t, J = 8.4 Hz, 2H), 1.40 (d, J = 6.8 Hz, 3H). 13 C NMR (101 MHz, CD 2Cl 2) δ , , , , , , , , , , , , 52.75, 47.67, 28.58, IR (ATR): 2970, 2842, 1605, 1484, 1255, 1071, 1007, 968, 742, 693 cm -1. HRMS calculated for C 18H 19BrN [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 12% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 3.6 min, t R2 (major) = 4.0 min. (R, E)-1-(4-(4-tolyl)but-3-en-2-yl)indoline (3ea) Colorless oil, 81% yield, 98% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ 7.26 (d, J = 8.0 Hz, 2H), 7.11 (d, J = 8.0 Hz, 2H), (m, 1H), (m, 1H), 6.58 (td, J = 7.5, 1.0 Hz, 1H), (m, 2H), 6.27 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), (m, 2H), 2.93 (t, J = 8.5 Hz, 2H), 2.31 (s, 3H), 1.39 (d, J S6
7 = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , 52.84, 47.63, 28.59, 21.26, IR (ATR): 2969, 2843, 1605, 1485, 1458, 1254, 1080, 969, 799, 743, 712 cm -1. HRMS calculated for C 19H 22N [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 4% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 3.7 min, t R2 (major) = 4.1 min. (R, E)-1-(4-(4-methoxyphenyl)but-3-en-2-yl)indoline (3fa) Colorless oil, 80% yield, 96% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 2H), (m, 2H), (m, 2H), 6.58 (td, J = 7.5, 1.0 Hz, 1H), (m, 2H), 6.19 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), 3.79 (s, 3H), (m, 2H), 2.94 (t, J = 8.5 Hz, 2H), 1.39 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , 55.63, 52.82, 47.59, 28.59, IR (ATR): 2969, 2834, 1605, 1509, 1486, 1246, 1173, 1032, 968, 737, 710 cm -1. HRMS calculated for C 19H 22NO [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 3% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 13.5 min, t R2 (major) = 14.2 min. (R, E)-1-(4-(3-chlorophenyl)but-3-en-2-yl)indoline (3ga) Colorless oil, 78% yield, 97% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (400 MHz, CD 2Cl 2) δ (m, 1H), (m, 2H), (m, 1H), (m, 2H), 6.59 (td, J = 7.2, 0.8 Hz, 1H), (m, 2H), 6.35 (dd, J = 16.0, 5.6 Hz, 1H), (m, 1H), (m, 2H), 2.94 (t, J = 8.4 Hz, 2H), 1.40 (d, J = 6.8 Hz, 3H). 13 C NMR (101 MHz, CDCl 3) δ , , , , , , , , , , , , , , 52.73, 47.67, 28.58, IR (ATR): 2970, 2842, 1605, 1485, 1256, 1182, 964, 877, 740, 684cm -1. HRMS calculated for C 18H 19ClN [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 7% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 4.1 min, t R2 (major) = 4.9 min. (R, E)-1-(4-(3-bromophenyl)but-3-en-2-yl)indoline (3ha) Colorless oil, 82% yield, 97% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (400 MHz, CD 2Cl 2) δ (m, 1H), (m, 1H), (m, 1H), 7.18 (t, J = 7.6 Hz, 1H), (m, 2H), (m, 1H), (m, 2H), 6.34 (dd, J = 16.0, 5.6 Hz, 1H), (m, 1H), (m, 2H), 2.94 (t, J = 8.4 Hz, 2H), 1.40 (d, J = 6.8 Hz, 3H). 13 C NMR (101 MHz, CDCl 3) δ , , , , , , , , , , , , , , 52.76, 47.67, 28.58, IR (ATR): 2970, 2842, 1605, 1485, 1257, 1182, 964, 867, 742, cm -1. HRMS calculated for C 18H 19BrN [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 3% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 10.1 min, t R2 (major) = 12.0 min. (R, E)-1-(4-(3-tolyl)but-3-en-2-yl)indoline (3ia) S7
8 Colorless oil, 80% yield, 96% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (400 MHz, CD 2Cl 2) δ (m, 3H), (m, 3H), (m, 3H), 6.31 (dd, J = 16.0, 5.6 Hz, 1H), (m, 1H), (m, 2H), 2.94 (t, J = 8.4 Hz, 2H), 2.33 (s, 3H), 1.40 (d, J = 6.8 Hz, 3H). 13 C NMR (101 MHz, CDCl 3) δ , , , , , , , , , , , , , , 52.82, 47.64, 28.59, 21.47, IR (ATR): 2922, 2850, 1605, 1486, 1255, 1052, 1023, 966, 742, 694 cm -1. HRMS calculated for C 19H 22N [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 7% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 3.5 min, t R2 (major) = 4.1 min. (R, E)-1-(4-(2-chlorophenyl)but-3-en-2-yl)indoline (3ja) Colorless oil, 73% yield, 93% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (400 MHz, CD 2Cl 2) δ 7.51 (dd, J = 7.6, 2.0 Hz, 1H), 7.35 (dd, J = 7.6, 1.6 Hz, 1H), (m, 2H), (m, 2H), 6.96 (dd, J = 16.0, 1.2 Hz, 1H), 6.60 (t, J = 7.2 Hz, 1H), (m, 1H), 6.31 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), (m, 2H), 2.95 (t, J = 8.4 Hz, 2H), 1.43 (d, J = 6.8 Hz, 3H). 13 C NMR (101 MHz, CD 2Cl 2) δ , , , , , , , , , , , , , , 52.95, 47.66, 28.60, IR (ATR): 2970, 2842, 1605, 1485, 1259, 966, 741, 694 cm -1. HRMS calculated for C 18H 19ClN [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 2% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 8.8 min, t R2 (major) = 9.9 min. (R, E)-1-(4-(2-tolyl)but-3-en-2-yl)indoline (3ka) Colorless oil, 69% yield, 96% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 1H), (m, 3H), (m, 2H), 6.78 (d, J = 16.0 Hz, 1H), 6.59 (t, J = 7.5 Hz, 1H), 6.54 (d, J = 7.5 Hz, 1H), 6.15 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), (m, 2H), 2.94 (t, J = 8.5 Hz, 2H), 2.31 (s, 3H), 1.42 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , , , 53.16, 47.63, 28.61, 19.93, IR (ATR): 2968, 2844, 1605, 1485, 1458, 1259, 1181, 967, 742, 711 cm -1. HRMS calculated for C 19H 22N [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 4% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 3.8 min, t R2 (major) = 4.4 min. (R, E)-1-(4-(furan-2-yl)but-3-en-2-yl)indoline (3la) Colorless oil, 78% yield, 95% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ 7.33 (s, 1H), (m, 2H), 6.59 (t, J = 7.5 Hz, 1H), 6.48 (d, J = 8.0 Hz, 1H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), 2.93 (t, J = 8.5 Hz, 2H), 1.38 (t, J = 6.5 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , 52.45, 47.54, 28.55, IR (ATR): 2970, 2844, 1605, 1485, 1254, 1150, 1011, 961, 732 cm -1. HRMS calculated for C 16H 18NO [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 2% i PrOH, 3.0 ml/min, 254 nm, 44 C, S8
9 nozzle pressure = 200 bar CO 2, t R1 (major) = 4.6 min, t R2 (minor) = 5.5 min. (R, E)-1-(4-(thiophen-2-yl)but-3-en-2-yl)indoline (3ma) Colorless oil, 73% yield, 92% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 1H), (m, 1H), (m, 1H), (m, 2H), 6.70 (dd, J = 16.0, 1.5 Hz, 1H), 6.60 (td, J = 7.5, 1.0 Hz, 1H), 6.49 (d, J = 8.0 Hz, 1H), 6.15 (dd, J = 16.0, 6.0 Hz, 1H), (m, 1H), (m, 2H), 2.94 (t, J = 8.5 Hz, 2H), 1.38 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , , , , , 52.60, 47.64, 28.59, IR (ATR): 2969, 2843, 1605, 1485, 1252, 1181, 955, 853, 742 cm -1. HRMS calculated for C 16H 18NS [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 2% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (major) = 8.4 min, t R2 (minor) = 9.3 min. (R, E)-1-(undec-3-en-2-yl)indoline (3na) Colorless oil, 68% yield, 76% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 2H), (m, 1H), 6.43 (d, J = 8.0 Hz, 1H), (m, 1H), 5.50 (dd, J = 15.5, 6.0 Hz, 1H), (m, 1H), (m, 2H), 2.89 (t, J = 8.5 Hz, 2H), (m, 2H), (m, 13H), 0.88 (t, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , 52.38, 47.24, 32.79, 32.23, 29.76, 29.52, 29.43, 28.46, 23.04, 16.55, IR (ATR): 2923, 2852, 1606, 1486, 1460, 1256, 1182, 1159, 970, 740 cm -1. HRMS calculated for C 19H 30N [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 10% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 1.9 min, t R2 (major) = 2.1 min. (R, E)-1-(pent-3-en-2-yl)indoline (3oa) Colorless oil, 73% yield, 75% ee, [ ] 24 D = (c 1.0, CH 2Cl 2). 1 H NMR (500 MHz, CD 2Cl 2) δ (m, 2H), 6.56 (t, J = 7.5 Hz, 1H), 6.43 (d, J = 7.5 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 2H), 2.89 (t, J = 8.5 Hz, 2H), (m, 3H), 1.26 (d, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl 3) δ , , , , , , , , 52.46, 47.24, 28.50, 17.97, IR (ATR): 2969, 2845, 1605, 1485, 1254, 1183, 1160, 964, 741, 710 cm -1. HRMS calculated for C 13H 18N [M+H] , found Chiral SFC: 250 mm CHIRALCEL IC, 0.5% i PrOH, 3.0 ml/min, 254 nm, 44 C, nozzle pressure = 200 bar CO 2, t R1 (minor) = 4.9 min, t R2 (major) = 5.2 min. 4. Synthesis of N-allylic indole 5 3 S9
10 To a solution of 3oa (18.7 mg, 0.10 mmol) in THF (1 ml) added DDQ (2,3-dichloro-5,6-dicyanop-benzoquinone, 25.0 mg, 0.11 mmol) and the reaction system was stirred for 10 min at room temperature. THF was removed and the pure allylic indole 5 was obtained by column chromatography (hexanes/etoac = 15:1) as a colorless oil (14.0 mg, 76% yield). [ ] 24 D = (c 1.0, CHCl 3) [lit. 3 [ ] 24 D = (c 1.0, CHCl 3) for R configuration, 39% ee]. 1 H NMR (400 MHz, CDCl 3) δ 7.64 (d, J = 7.6 Hz, 1H), 7.38 (d, J = 8.4 Hz, 1H), (m, 2H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), 1.69 (dt, J = 6.0, 1.2 Hz, 3H), 1.62 (d, J = 6.8 Hz, 3H). 13 C NMR (101 MHz, CDCl 3) δ , , , , , , , , , , 52.60, 20.40, References 1) Preuß, T.; Saak, W.; Doye, S. Chem. Eur. J. 2013, 19, ) Chen, Q.-A.; Chen, Z.; Dong, V. M. J. Am. Chem. Soc. 2015, 137, ) Zhao, Q.; Zhuo, C.-X.; You, S.-L. RSC Adv. 2014, 4, S10
11 6. NMR spectra (E)-2-(4-(4-methoxyphenyl)but-3-en-2-yl)-1,3-diphenylpropane-1,3-dione S11
12 (E)-1-methoxy-4-(3-(3-phenylpropoxy)but-1-en-1-yl)benzene S12
13 (E)-(4-(4-methoxyphenyl)but-3-en-2-yl)(4-tolyl)sulfane S13
14 (R, E)-4-chloro-1-(4-phenylbut-3-en-2-yl)indoline (3ab) S14
15 (R, E)-4-methyl-1-(4-phenylbut-3-en-2-yl)indoline (3ac) S15
16 (R, E)-4-methoxy-1-(4-phenylbut-3-en-2-yl)indoline (3ad) S16
17 (R, E)-5-fluoro-1-(4-phenylbut-3-en-2-yl)indoline (3ae) S17
18 (R, E)-5-chloro-1-(4-phenylbut-3-en-2-yl)indoline (3af) S18
19 (R, E)-5-bromo-1-(4-phenylbut-3-en-2-yl)indoline (3ag) S19
20 (R, E)-5-methoxy-1-(4-phenylbut-3-en-2-yl)indoline (3ah) S20
21 (R, E)-6-methyl-1-(4-phenylbut-3-en-2-yl)indoline (3ai) S21
22 (R, E)-6-methoxy-1-(4-phenylbut-3-en-2-yl)indoline (3aj) S22
23 (R, E)-1-(4-(4-fluorophenyl)but-3-en-2-yl)indoline (3ba) S23
24 (R, E)-1-(4-(4-chlorophenyl)but-3-en-2-yl)indoline (3ca) S24
25 (R, E)-1-(4-(4-bromophenyl)but-3-en-2-yl)indoline (3da) S25
26 (R, E)-1-(4-(4-tolyl)but-3-en-2-yl)indoline (3ea) S26
27 (R, E)-1-(4-(4-methoxyphenyl)but-3-en-2-yl)indoline (3fa) S27
28 (R, E)-1-(4-(3-chlorophenyl)but-3-en-2-yl)indoline (3ga) S28
29 (R, E)-1-(4-(3-bromophenyl)but-3-en-2-yl)indoline (3ha) S29
30 (R, E)-1-(4-(3-tolyl)but-3-en-2-yl)indoline (3ia) S30
31 (R, E)-1-(4-(2-chlorophenyl)but-3-en-2-yl)indoline (3ja) S31
32 (R, E)-1-(4-(2-tolyl)but-3-en-2-yl)indoline (3ka) S32
33 (R, E)-1-(4-(furan-2-yl)but-3-en-2-yl)indoline (3la) S33
34 (R, E)-1-(4-(thiophen-2-yl)but-3-en-2-yl)indoline (3ma) S34
35 (R, E)-1-(undec-3-en-2-yl)indoline (3na) S35
36 (R, E)-1-(pent-3-en-2-yl)indoline (3oa) S36
37 7. SFC spectra 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
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