Supporting Information. Asymmetric Binary-acid Catalysis with Chiral. Phosphoric Acid and MgF 2 : Catalytic
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1 Supporting Information Asymmetric Binary-acid Catalysis with Chiral Phosphoric Acid and MgF 2 : Catalytic Enantioselective Friedel-Crafts Reactions of β,γ- Unsaturated-α-Ketoesters Jian Lv, Xin Li, Long Zhang, Sanzhong Luo,* Jin-Pei Cheng Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, the Chinese Academy of Sciences, Beijing , China luosz@iccas.ac.cn General Information: Commercial reagents were used as received, unless otherwise indicated. 1 H, 13 C, NMR spectra were measured on a NMR instrument (300 MHz for 1 H NMR, 75 MHz for 13 C NMR). Tetramethylsilane (TMS) served as the internal standard for 1 H NMR, and CD 3 served as the internal standard for 13 C NMR. The following abbreviations were used to express the multiplicities: s = singlet; d= doublet; t = triplet; q 1
2 = quartet; m = multiplet; br = broad. HPLC analysis was performed using Chiralcel columns purchased. General Procedure for Asymmetric Friedel-Crafts Alkylation of β,γ-unsaturated-α- Ketonesters: To a flame-dried Schlenk tube was added MgF 2 (0.005 mmol, 5 mol%), (S)-1a (0.020 mmol, 20 mol%) and 4 Ǻ M.S. (40 mg). The mixture was dried under vacuum for 0.5 h and distilled anhydrous CH 2 2 (1.5 ml) was added under Ar. After stirring for 0.5 h, 3a (0.10 mmol) in CH 2 2 (0.25 ml) was added and the mixture were cooled to -70 C. After addition of 2a (0.12 mmol) in CH 2 2 (0.25 ml), the mixture was stirred for 48 h at -70 C. Purification of the mixture by column chromatography on silica gel with DCM-ethyl acetate (25:1) as eluent gave 4a as a colorless oil (24.8 mg, 79%). The enantiomeric ratios of the product were determined by chiral HPLC analysis using a chiral column. Compound 4k, 1 4o, 2 4q 1 and 4r 1 are known compounds. The absolute configurations of other products including the phenol products are determined by analogy with these known compounds. Yield: 79%; [α] D 25 = (c = 0.45, CH 2 2 ); 1 H NMR (300 MHz, H CD 3 ): δ (m, 5 H), 6.88 (d, J = 8.2 Hz, 1 H), 6.35 (d, J = 2.4 4a Hz, 1 H), 6.29 (dd, J = 8.1, 2.4 Hz, 1 H), 5.52 (br, 1 H), 4.93 (dd, J = 7.6, 7.6 Hz, 1 H), 3.83 (s, 3 H), 3.70 (s, 3 H), 3.63 (dd, J = 16.8, 7.2 Hz, 1 H), 3.47 (dd, J = 16.8, 7.8 Hz, 1 H), (m, 2 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.8, 161.3, 157.7, 155.7, 143.0, 128.8, 128.4, 127.9, 126.4, 123.5, 106.9, 99.1, 55.3, 53.0, 44.7, 38.7 ppm; IR (KBr, cm -1 ): 3445, 3084, 3060, 3029, 3004, 2954, 2839, 1731, 1615, 1597, 1507, 1496, 1469, 1455, 1433, 1397, 1280, 1239, 1157, 1112, 1069, 1034, 957, 834, 762, 734, 2
3 701, 635, 558; HRMS (EI-TF) calcd for C 18 H 18 5 : , found ; HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 9:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 25.9 min (minor) and 29.4 min (major). Et Yield: 80%; [α] D 25 = +5.9 (c = 0.91, CH 2 2 ); 1 H NMR (300 MHz, H Me CD 3 ): δ (m, 5 H), 6.86 (d, J = 8.0 Hz, 1 H), (m, 2 4b H), 4.82 (dd, J = 7.6, 7.6 Hz, 1 H), (m, 2 H), 3.73 (s, 3 H), (m, 2 H), 1.27 (t, J = 7.0 Hz, 3 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 191.7, 160.4, 156.3, 154.5, 142.2, 127.6, 127.3, 127.0, 125.3, 122.9, 105.7, 98.9, 62.7, 52.0, 43.3, 38.0, 13.7 ppm; IR (KBr, cm -1 ): 3451, 3029, 2978, 1729, 1612, 1596, 1507, 1478, 1452, 1394, 1277, 1235, 1173, 1117, 1068, 1039, 991, 897, 822, 732, 700, 634, 547; HRMS (EI-TF) calcd C 19 H 20 5 : , found ; HPLC analysis: Daicel Chiralpak AS-H, hexane/iso-propanol = 9:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 25.2 min (major) and 27.8 min (minor). Yield: 70%; [α] D 25 = (c = 1.27, CH 2 2 ); 1 H NMR (300 MHz, H CD 3 ): δ (m, 4 H), 6.88 (d, J = 8.2 Hz, 1 H), 6.36 (d, J = 4c 2.4 Hz, 1 H), 6.32 (dd, J = 2.4, 8.4 Hz, 1 H), (m, 2 H), 3.82 (s, 3 H), 3.72 (s, 3 H), 3.57 (dd, J = 7.8, 17.1 Hz, 1 H), 3.44 (dd, J = 7.2, 17.1 Hz, 1 H), ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.3, 161.3, 157.8, 155.7, 141.6, 132.0, 129.3, 128.6, 128.4, 123.4, 106.9, 99.2, 55.3, 53.0, 44.3, 38.2 ppm; IR (KBr, cm -1 ): 3449, 3030, 3005, 2954, 2838, 1729, 1614, 1596, 1507, 1490, 1468, 1456, 1433, 1408, 1281, 1237, 1197, 1157, 1114, 1089, 1033, 1014, 9956, 834, 737; HRMS (EI-TF) calcd for C 18 H 17 5 : , found ; HPLC analysis: Daicel Chiralpak AD-H, 3
4 hexane/iso-propanol = 9:1, flow rate = 1.0 ml/min, λ = 254 nm, retention time: 32.0 min (minor) and 41.0 min (major). Et Yield: 65%; [α] D 25 = (c = 0.95, CH 2 2 ); 1 H NMR (300 MHz, H CD 3 ): δ (m, 4 H), 6.95 (d, J = 7.9 Hz, 1 H), (m, 4d 2 H), (m, 2 H), (m, 2 H), 3.83 (s, 3 H), 3.60 (dd, J = 8.1, 17.4 Hz, 1 H), 3.52 (dd, J = 7.5, 16.5 Hz, 1 H), 1.36 (t, J = 7.0 Hz, 3 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.4, 161.3, 157.2, 155.6, 141.8, 131.9, 129.3, 128.4, 128.3, 123.3, 106.6, 99.9, 63.7, 53.0, 44.1, 38.4, 14.7 ppm; IR (KBr, cm -1 ): 3451, 3031, 2978, 2953, 2926, 2853, 1730, 1613, 1594, 1507, 1490, 1453, 1395, 1279, 1236, 1175, 1117, 1089, 1072, 1039, 1014, 992, 973, 897, 835, 822, 740, 633, 593, 552; HRMS (EI-TF) calcd for C 19 H 19 5 : , found ; HPLC analysis: Daicel Chiralpak AD- H, hexane/iso-propanol = 9:1, flow rate = 1.0 ml/min, λ = 219 nm, retention time: 22.0 min (minor) and 27.6 min (major). Yield: 81%; [α] D 25 = (c = 0.59, CH 2 2 ); 1 H NMR (300 MHz, H 4e CD 3 ): δ (m, 2 H), 7.07 (dd, J = 2.1, 8.3 Hz, 1 H), 6.90 (d, J = 8.1 Hz, 1 H), 6.36 (d, J = 2.4 Hz, 1 H), 6.33 (dd, J = 2.4, 8.1 Hz, 1 H), 5.00 (br, 1H), 4.83 (dd, J = 7.6, 7.6 Hz, 1 H), 3.83 (s, 3 H), 3.72 (s, 3 H), 3.56 (dd, J = 7.8, 17.4 Hz, 1 H), 3.46 (dd, J = 6.3, 17.4 Hz, 1 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.0, 161.2, 157.8, 155.9, 143.7, 132.3, 130.2, 129.9, 128.5, 127.4, 122.6, 107.0, 99.4, 55.4, 53.0, 44.1, 38.1 ppm; IR (KBr, cm -1 ): 3452, 3006, 2954, 2839, 1730, 1615, 1597, 1508, 1469, 1433, 1401, 1286, 1237, 1198, 1159, 1114, 1073, 1030, 1014, 997, 821, 737, 701, 650, 636, 573, 547; HRMS (EI-TF) calcd for C 18 H : , found 4
5 ; HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 9:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 26.2 min (minor) and 29.1 min (major). Yield: 76%; [α] D 25 = +2.2 (c = 0.55, CH 2 2 ); 1 H NMR (300 MHz, H Et CD 3 ): δ (m, 2 H), 7.00 (dd, J = 1.9, 8.3 Hz, 1 H), 6.83 (d, J 4f = 8.1 Hz, 1 H), 6.29 (d, J = 2.1 Hz, 1 H), 6.26 (dd, J = 2.4, 8.4 Hz), 4.91 (br, 1 H), 4.76 (dd, J = 7.6, 7.6 Hz, 1 H), 4.21 (q, J = 7.15 Hz, 2 H), 3.65 (s, 3 H), 3.48 (dd, J = 7.8, 17.4 Hz, 1 H), 3.38 (dd, J =7.2, 17.4 Hz, 1 H), 1.26 (t, J = 7.14 Hz, 3 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.4, 160.8, 157.8, 155.9, 143.6, 132.2, 130.2, 130.1, 129.9, 128.5, 127.4, 122.6, 107.0, 99.3, 62.6, 55.4, 44.0, 38.1, 14.0 ppm; IR (KBr, cm -1 ): 3436, 3034, 2961, 2932, 2867, 2843, 1726, 1614, 1596, 1562, 1508, 1467, 1432, 1400, 1369, 1261, 1233, 1195, 1157, 1072, 1030, 957, 803, 737, 703, 677, 606, 506; HRMS (EI-TF) calcd for C 19 H , found ; HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 9:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 17.8 min (minor) and 19.8 min (major). H F 4g Yield: 82%; [α] D 25 = (c = 1.37, CH 2 2 ); 1 H NMR (300 MHz, CD 3 ): δ (m, 2 H), (m, 2 H), 6.91 (d, J = 8.2 Hz, 1 H), 6.36 (d, J = 2.1 Hz, 1 H), 6.31 (dd, J = 2.4, 8.1 Hz, 1 H), 5.1 (dd, J = 7.6, 7.6 Hz, 1 H), 4.95 (br, 1H), 3.83 (s, 3 H), 3.73 (s, 3 H), 3.58 (dd, J = 6.5, 16.0 Hz, 1 H), 3.51 (dd, J = 6.7, 16.0 Hz, 1 H), ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.2, 161.3, 157.9, 155.7, 129.3, 129.2, 128.8, 128.1, 128.0, 123.9, 123.8, 122.2, 115.7, 115.4, 106.8, 99.2, 55.4, 52.9, 43.6, 33.1 ppm; IR (KBr, cm -1 ): 3450, 3040, 3008, 2955, 2840, 1730, 1615, 1598, 1508, 1490, 1468, 1455, 1433, 1408, 1277, 1230, 1199, 1158, 1112, 1071, 5
6 1035, 957, 834, 759, 635, 571; HRMS (EI-TF) calcd for C 18 H 17 F 5 : , found ; HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 9:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 27.0 min (major) and 29.0 min (minor). Me Yield: 57%; [α] D 25 = +4.5 (c = 0.85, CH 2 2 ); 1 H NMR (300 MHz, H Me CD 3 ): δ 7.1 (m, 4 H), 6.88 (d, J = 8.2 Hz, 1 H), 6.35 (d, J = 2.4, 1 Me 4h H), 6.29 (dd, J = 2.4, 8.2 Hz, 1H), 4.88 (dd, J = 7.6, 7.6 Hz, 1 H), 4.85 (br, 1H), 3.81 (s, 3 H), 3.73 (s, 3 H), 3.57 (dd, J = 7.6, 16.6, 1 H), 3.42 (dd, J= 7.7, 16.6, 1 H), 2.29 (s, 3 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.6, 161.4, 157.7, 155.4, 140.0, 135.8, 129.1, 128.8, 127.8, 124.1, 106.8, 99.1, 55.3, 52.9, 44.7, 38.3, 21.0 ppm; IR (KBr, cm -1 ): 3450, 3024, 3006, 2953, 2925, 2838, 1730, 1614, 1597, 1507, 1468, 1433, 1278, 1238, 1197, 1157, 1119, 1072, 1034, 997, 832, 738, 635, 560; HRMS (EI-TF) calcd for C 19 H 20 5 : , found ; HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 9:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 24.3 min (major) and 29.9 min (minor). Me Yield: 75%; [α] D 25 = -5.8 (c = 0.50, CH 2 2 ); 1 H NMR (300 MHz, Me H Me CD 3 ): δ (m, 4 H), 6.90 (d, J = 8.2 Hz, 1 H), 6.37 (d, J = 4i H), 6.32 (dd, J = 2.4, 8.2 Hz, 1 H), (m, 2 H), 3.84 (s, 3 H), 3.75 (s, 3 H), 3.60 (dd, J = 7.4, 16.6 Hz, 1 H), 3.44 (dd, J = 7.8, 16.6 Hz, 1 H), 2.32 (s, 3 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.6, 161.4, 157.7, 155.4, 142.9, 137.9, 128.9, 128.7, 128.2, 127.1, 124.9, 123.8, 106.9, 99.1, 55.3, 52.9, 44.7, 38.6, 21.5 ppm; IR (KBr, cm -1 ): 3449, 3008, 2953, 2922, 2839, 1729, 1613, 1599, 1507, 1467, 1433, 1408, 1279, 1243, 1197, 1157, 1110, 1072, 1034, 956, 834, 737, 702, 636; HRMS (EI-TF) 6
7 calcd C 19 H 20 5 : , found ; HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 9:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 18.0 min (minor) and 19.8 min (major). Me Yield: 59%; [α] D 25 = +6.6 (c = 0.70, CH 2 2 ); 1 H NMR (300 MHz, H Me CD 3 ): δ 7.58 (d, J = 7.3 Hz, 2 H), 7.52 (d, J = 8.2 Hz, 2 H), Ph 4j 7.32 (m, 5 H), 6.96 (d, J = 8.2 Hz, 1 H), 6.39 (d, J = 2.3, 1 H), 6.34 (dd, J = 2.4, 8.2 Hz, 1 H), (m, 2 H), 3.85 (s, 3 H), 3.75 (s, 3 H), 3.67 (dd, J= 7.6, 16.8 Hz, 1 H), 3.51 (dd, J = 7.7, 16.8 Hz, 1 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.6, 161.3, 157.8, 155.6, 142.2, 140.9, 139.2, 128.8, 128.7, 128.3, 127.1, 127.0, 123.7, 123.6, 107.0, 99.2, 55.4, 53.0, 44.6, 38.4 ppm; IR (KBr, cm -1 ): 3452, 3028, 2955, 2851, 1730, 1614, 1597, 1506, 1486, 1467, 1454, 1433, 1408, 1280, 1236, 1197, 1157, 1109, 1173, 1033, 1009, 857, 836, 803, 766, 738, 698, 634, 569, 553, 509; HRMS (EI-TF) calcd C 24 H 22 5 : , found ; HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 9:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 51.4 min (minor) and 57.8 min (major). 4k Me Yield: 82%; [α] D 25 = (c = 0.50, CH 3 ) ([α] D 25 = (c = 1.00, CH 3 for 99.5% ee (R) in ref. 1); 1 H NMR (300 MHz, CD 3 ): δ 8.01 (br, 1 H), 7.42 (d, J = 7.9 Hz, 1 H), (m, 9 H), 4.92 (dd, J = 7.5, 7.5 Hz, 1 H), 3.76 (s, 3 H), 3.69 (dd, J = 7.3, 17.0 Hz, 1 H), 3.60 (dd, J = 7.8, 17.0 Hz, 1 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.6, 161.3, 143.2, 136.6, 128.5, 127.8, 126.6, 122.3, 121.5, 119.6, 119.4, 118.4, 111.1, 52.9, 45.7, 37.7 ppm; HPLC analysis: Daicel 7
8 Chiralpak AD-H, hexane/iso-propanol = 4:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 12.7 min (major) and 14.9 min (minor). Yield: 87%; [α] D 25 = -8.8 (c = 0.40, CH 2 2 ); 1 H NMR (300 MHz, F 4l Me CD 3 ): δ 8.03 (br, 1 H), 7.49 (d, J = 8.0 Hz, 1 H), 7.33 (d, J = 8.1, 1 H), (m, 7 H), 5.22 (dd, J = 7.6, 7.6 Hz, 1 H), 3.80 (s, 3 H), 3.77 (dd, 10.5, 20.1 Hz, 1 H), 3.60 (dd, J = 7.5, 17.2, 1 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.2, 161.2, 158.9, 136.4, 129.9, 129.4, 129.3, 128.3, 128.2, 126.4, 124.2, 124.1, 122.4, 121.7, 119.7, 119.2, 117.0, 115.8, 115.5, 111.2, 53.0, 44.4, 31.0 ppm; IR (KBr, cm -1 ): 3411, 3057, 2953, 2919, 1731, 1646, 1618, 1584, 1488, 1457, 1420, 1401, 1339, 1272, 1255, 1230, 1099, 1011, 968, 943, 825, 746, 701, 621, 611,586 cm -1 ; HRMS (EI-TF) calcd for C 19 H 16 FN 3 : , found ; HPLC analysis: Daicel Chiralpak AS- H, hexane/iso-propanol = 4:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 9.5 min (major) and 10.2 min (minor). Yield: 82%; [α] D 25 = (c = 0.65, CH 2 2 ); 1 H NMR (300 MHz, 4m Me CD 3 ): δ 8.00 (br, 1 H), (m, 9 H), 4.89 (dd, J = 7.6, 7.6 Hz, 1 H), 3.78 (s, 3 H), 3.67 (dd, J = 7.1, 17.2 Hz, 1 H), 3.57 (dd, J = 8.0, 17.2, 1 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.3, 161.2, 141.7, 136.6, 132.3, 129.2, 128.6, 122.5, 121.4, 119.7, 119.3, 117.9, 111.2, 53.0, 45.5, 37.1 ppm; IR (KBr, cm -1 ): 3410, 3056, 2953, 2922, 2851, 1731, 1671, 1619, 1576, 1558, 1541, 1521, 1490, 1457, 1434, 1420, 1338, 1253, 1253, 1120, 1127, 1091, 1064, 1013, 967, 930, 876, 832, 764, 743, 657, 582; HRMS (EI-TF) calcd for C 19 H 16 N 3 : , found ; 8
9 HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 4:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 13.2 min (major) and 20.4 min (minor). Yield: 80%; [α] D 25 = (c = 1.09, CH 2 2 ); 1 H NMR (300 MHz, 4n Me CD 3 ): δ 7.99 (br, 1 H), (m, 8 H), 4.80 (dd, J = 7.4, 7.4 Hz, 1 H), 3.73 (s, 3 H), 3.60 (dd, J = 7.0, 17.5 Hz, 1 H), 3.49 (dd, J = 8.0, 17.5 Hz, 1 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 190.8, 160.1, 142.6, 135.5, 131.5, 129.6, 129.4, 128.7, 126.3, 125.0, 121.6, 120.4, 118.8, 118.1, 116.2, 110.3, 52.1, 44.2, 35.8 ppm; IR (KBr, cm -1 ): 3416, 3062, 2963, 2893, 2830, 1729, 1621, 1593, 1561, 1469, 1397, 1338, 1260, 1094, 1063, 1030, 801, 742, 709, 676, 588, 504; HRMS (EI-TF) calcd for C 19 H 15 2 N 3 : , found ; HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 4:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 10.6 min (major) and 13.2 min (minor). Yield: 78%; [α] D 25 = (c = 0.59, CH 3 ) ([α] D 25 = (c = Me 1.00, CH 3 for 90% ee in ref. [2]]; 1 H NMR (300 MHz, CD 3 ): δ Me 4o 7.99 (br, 1 H), 7.43 (d, J = 7.92 Hz, 1 H), 7.31 (d, J = 8.12 Hz, 1 H), (m, 7 H), 4.88 (dd, J = 7.6, 7.6 Hz, 1 H), 3.76 (s, 3 H), 3.67 (dd, J =7.3, 16.9 Hz, 1 H), 3.57 (dd, J = 7.9, 16.9 Hz, 1 H), 2.28 (s, 3 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 193.0, 161.7, 140.5, 136.9, 136.4, 129.5, 127.9, 126.7, 122.6, 121.8, 119.8, 119.7, 118.9, 111.4, 53.2, 46.1, 37.7, 21.3 ppm; HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 4:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 14.4 min (major) and 18.3 min (minor). 9
10 Yield: 81%; [α] D 25 = -3.8 (c = 0.80, CH 2 2 ); 1 H NMR (300 MHz, CD 3 ): δ 7.99 (br, 1 H), (m, 11 H), (m, 3 H), Ph 4p 4.97 (dd, J = 7.5, 7.5 Hz, 1 H), 3.78 (s, 3 H), (m, 2 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.6, 161.3, 148.0, 142.3, 140.8, 139.5, 136.6, 128.7, 128.2, 127.3, 127.1, 127.0, 122.4, 121.5, 119.6, 119.5, 118.3, 111.2, 53.0, 45.6, 37.4 ppm; IR (KBr, cm -1 ): 3419, 3054, 3029, 2951, 2924, 2851, 1729, 1618, 1600, 1548, 1518, 1486, 1457, 1434, 1418, 1338, 1278, 1265, 1253, 1238, 1199, 1127, 1065, 1007, 967, 875, 839, 762, 742, 698, 585, 554, 510; HRMS (EI-TF) calcd for C 25 H 21 N 3 : , found ; HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 4:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 18.5 min (major) and 22.9 min (minor). 4q Yield: 90%; [α] 25 D = +4.7 (c = 0.82, CH 3 ) ([α] 25 D = +5.2 (c = 1.00, CH 3 for 99.5% ee (R) in ref. 1); 1 H NMR (300 MHz, CD 3 ): δ 7.92 (br, 1 H), (m, 6 H), 7.00 (d, J = 2.2 Hz, 1 H), (m, 2 H), 4.86 (dd, J = 7.5, 7.5 Hz, 1 H), 3.77 (s, 3 H), 3.74 (s, 3 H), 3.68 (dd, J = 7.3, 17.0 Hz, 1 H), 3.59 (dd, J = 7.8, 17.0 Hz, 1 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.6, 161.3, 153.9, 143.1, 131.7, 128.6, 127.8, 126.8, 126.6, 122.2, 118.1, 112.4, 111.8, 101.3, 55.8, 53.0, 45.6, 37.7 ppm; HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 4:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 13.3 min (major) and 19.5 min (minor). Yield: 83%; [α] D 25 = (c = 0.84, CH 3 ) ([α] D 25 = (c = 1.00, CH 3 for 97% ee (R) in ref. 1); 1 H NMR (300 MHz, CD 3 ): δ r 10
11 (br, 1 H), (m, 7 H), 7.03 (d, J = 2.3 Hz, 1 H), 6.97 (dd, J = 1.67, 8.5 Hz, 1 H), 4.87 (dd, J = 7.5, 7.5 Hz, 1 H), 3.78 (s, 3 H), 3.67 (dd, J = 7.5, 17.1 Hz, 1 H), 3.57 (dd, J = 7.6, 17.0 Hz, 1 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 192.4, 161.3, 142.9, 136.9, 128.6, 128.3, 127.7, 126.8, 125.0, 122.1, 120.3, 118.5, 111.1, 53.0, 45.6, 37.6 ppm; HPLC analysis: Daicel Chiralpak AD-H, hexane/iso-propanol = 4:1, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 15.1 min (minor) and 16.9 min (major). Yield: 64%; [α] D 25 = (c = 0.50, CH 2 2 ); 1 H NMR (300 MHz, CD 3 ): δ 8.08 (br, 1 H), (m, 7 H), 4.83 (dd, J = 7.4, 7.4 Hz, 4s 1 H), 3.82 (s, 3 H), 3.68 (dd, J = 7.0, 17.6 Hz,1 H), 3.56 (dd, J=7.8, 17.6 Hz,1 H) ppm; 13 C NMR (75 MHz, CD 3 ): δ 191.7, 161.1, 143.3, 136.9, 132.6, 130.8, 130.5, 129.7, 128.7, 127.2, 124.7, 122.1, 120.6, 120.0, 117.4, 111.3, 53.1, 45.2, 36.6 ppm; IR (KBr, cm -1 ): 3393, 3068, 2987, 2920, 2849, 1729, 1646, 1467, 1396, 1335, 1249, 1131, 1062, 1029, 907, 802, 703, 651, 613; HRMS (EI-TF) calcd for C 19 H 14 3 N 3 : , found ; HPLC analysis: Daicel Chiralpak J-H, hexane/iso-propanol = 70:30, flow rate = 1.0 ml/min, λ = 210 nm, retention time: 26.2 min (minor) and 38.0 min (major). Reference [1] Jensen, K. B.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. Angew Chem. Int. Chem. 2001, 40, 160. [2] Desimoni, G.; Faita, G.; Toscanini, M.; Boiocchi, M. Chem. Eur. J. 2008, 14,
12 H 4a H 4a 12
13 H 4a H 4a 13
14 Et H Me 4b Et H Me 4b 14
15 Et H Me 4b Et H Me 4b 15
16 H 4c H 4c 16
17 H 4c H 4c 17
18 Et H 4d Et H 4d 18
19 Et H 4d Et H 4d 19
20 H 4e H 4e 20
21 H 4e H 4e 21
22 H Et 4f H Et 4f 22
23 H Et 4f H Et 4f 23
24 H F 4g H F 4g 24
25 H F 4g H F 4g 25
26 Me H Me Me 4h Me H Me Me 4h 26
27 Me H Me Me 4h Me H Me Me 4h 27
28 Me Me H Me 4i Me Me H Me 4i 28
29 Me Me H Me 4i Me Me H Me 4i 29
30 Me H Me Ph 4j Me H Me Ph 4j 30
31 Me H Me Ph 4j Me H Me Ph 4j 31
32 Me 4k Me 4k 32
33 Me 4k Me 4k 33
34 F Me 4l F Me 4l 34
35 F Me 4l F Me 4l 35
36 Me 4m Me 4m 36
37 Me 4m Me 4m 37
38 Me 4n Me 4n 38
39 Me 4n Me 4n 39
40 Me Me 4o Me Me 4o 40
41 Me Me 4o Me Me 4o 41
42 Ph 4p Ph 4p 42
43 Ph 4p Ph 4p 43
44 4q 4q 44
45 4q 4q 45
46 4r 4r 46
47 4r 4r 47
48 4s 4s 48
49 4s 4s 49
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