Tao Liu, Ling‐Yan Chen, Zhihua Sun
Jan 29, 2016
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Influential Citations
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Journal
The Journal of organic chemistry
Abstract
P 11444. We regret that there were unintentional nomenclature errors in the title of the compounds. The first “R” in the names of compound 7a−r should be changed to “S” as follows: (S)-2-Methyl-N-((R)-1-phenylethyl)propane-2-sulfinamide (7a). A colorless oil (50.6 mg, 90%). H NMR (400 MHz, CDCl3) δ 7.30−7.36 (m, 5H), 4.57 (m, 1 H), 3.46 (s, 1H), 1.53 (d, J = 6.4 Hz, 3H), 1.26 (s, 9H). C NMR (100 MHz, CDCl3) δ 144.1, 128.7, 127.8, 126.6, 55.5, 54.0, 22.8, 22.6. (S)-2-Methyl-N-((R)-1-p-tolylethyl)propane-2-sulfinamide (7b). A colorless oil (52.0 mg, 87%). H NMR (400 MHz, CDCl3) δ 7.26 (d, J = 8.0 Hz, 2H), 7.17 (d, J = 7.6 Hz, 2H), 4.54 (m, 1H), 3.42 (s, 1H), 2.36 (s, 3H), 1.51 (d, J = 6.8 Hz, 3H), 1.25 (s, 9H). C NMR (100 MHz, CDCl3) δ 114.2, 137.5, 129.4, 126.5, 55.4, 53.7, 22.7, 22.6, 21.1. HRMS (ESITOF) m/z: [M + H] calcd for C13H21NOS 240.1417, found 240.1427. (S)-N-((R)-1-(4-Methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide (7c). A colorless oil (56.1 mg, 88%). H NMR (400 MHz, CDCl3) δ 7.29 (d, J = 7.6 Hz, 2H), 6.90 (d, J = 8.8 Hz, 2H), 4.53 (m, 1H), 3.82 (s, 3H), 3.43 (s, 1H), 1.51 (d, J = 6.4 Hz, 3H), 1.25 (s, 9H). C NMR (100 MHz, CDCl3) δ 159.2, 136.2, 127.7, 114.1, 55.4, 55.3, 53.4, 22.7, 22.6. (S)-N-((R)-1-(4-Chlorophenyl)ethyl)-2-methylpropane2-sulfinamide (7d). A colorless oil (57.8 mg, 89%). H NMR (400 MHz, CDCl3) δ 7.26−7.38 (m, 4H), 4.53 (m, 1H), 3.41 (s, 1H), 1.50 (d, J = 6.8 Hz, 3H), 1.25 (s, 9H). C NMR (100 MHz, CDCl3) δ 142.5, 133.5, 128.9, 128.0, 55.6, 53.5, 22.8, 22.6. HRMS (ESI-TOF) m/z: [M + H] calcd for C12H18ClNOS 260.0870, found 260.0880. (S)-2-Methyl-N-((R)-1-(4-(trifluoromethyl)phenyl)ethyl)propane-2-sulfinamide (7e). A colorless oil (60.1 mg, 82%). H NMR (400 MHz, CDCl3) δ 7.63 (d, J = 8.4 Hz, 2H), δ 7.49 (d, J = 8.4 Hz, 2H), 4.62 (m, 1H), 3.47 (d, J = 2.0 Hz, 1H), 1.55 (d, J = 6.4 Hz, 3H), 1.26 (s, 9H). C NMR (100 MHz, CDCl3) δ 148.0, 127.0, 125.7, 125.7, 55.7, 53.9, 22.9, 22.5. (S)-N-((R)-1-(4-Cyanophenyl)ethyl)-2-methylpropane2-sulfinamide (7f). A colorless oil (59.5 mg, 95%). H NMR (400 MHz, CDCl3) δ 7.62 (d, J = 8.4 Hz, 2H), 7.47 (d, J = 8.4 Hz, 2H), 4.58 (m, 1H), 3.59 (d, J = 3.6 Hz, 1H), 1.51 (d, J = 6.4 Hz, 3H), 1.22 (s, 9H). C NMR (100 MHz, CDCl3) δ 149.3, 132.6, 127.4, 118.6, 111.6, 55.8, 54.1, 22.9, 22.5. (S)-N-((R)-1-(3-Fluorophenyl)ethyl)-2-methylpropane2-sulfinamide (7g). A colorless oil (52.3 mg, 86%). H NMR (400 MHz, CDCl3) δ 6.97−7.28 (m, 4H), 4.56 (m, 1H), 3.48 (s, 1H), 1.52 (d, J = 6.8 Hz, 3H), 1.26 (s, 9H). C NMR (100 MHz, CDCl3) δ 163.0 (d, J = 245.0 Hz), 146.7 (d, J = 7.0 Hz), 130.3 (d, J = 8.0 Hz), 122.3 (d, J = 3.0 Hz), 114.7 (d, J = 21.0 Hz), 113.4 (d, J = 22.0 Hz), 55.6, 53.6, 22.8, 22.6. HRMS (ESITOF) m/z: [M + H] calcd for C12H18FNOS 244.1166, found 244.1174. (S)-2-Methyl-N-((R)-1-phenylpropyl)propane-2-sulfinamide (7h). A colorless oil (50.9 mg, 85%)> H NMR (400 MHz, CDCl3) δ 7.30−7.36 (m, 5H), 4.31 (m, 1H), 3.41 (s, 1H), 1.80 (m, 2H), 1.25 (s, 9H), 0.81 (t, J = 14.8 Hz, 3H). C NMR (100 MHz, CDCl3) δ 142.3, 128.6, 127.8, 127.3, 60.4, 55.7, 29.4, 22.6, 22.5. (S)-N-((R)-1-(4-Methoxyphenyl)-2,2-dimethylpropyl)2-methylpropane-2-sulfinamide (7i). A colorless oil (55.8 mg, 75%). H NMR (400 MHz, CDCl3) δ 7.96 (d, J = 8.4 Hz, 2H), 6.85 (d, J = 8.4 Hz, 2H), 3.81 (d, J = 8.0 Hz, 1H), 3.60 (s, 3H), 3.11 (s, 1H), 1.24 (s, 9H), 0.95 (s, 9H). C NMR (100 MHz, CDCl3) δ 159.0, 130.6, 129.2, 113.0, 66.5, 55.8, 55.1, 36.3, 26.7, 22.6. HRMS (ESI-TOF) m/z: [M + H] calcd for C16H27NO2S 298.1835, found 298.1828. (S)-N-((R)-(2-Hydroxyphenyl) (phenyl)methyl)-2-methylpropane-2-sulfinamide (7j). A colorless oil (39.4 mg, 52%). H NMR (400 MHz, CDCl3) δ 6.73−7.43 (m, 9H), 5.82 (d, J = 4.8 Hz, 1H), 5.06 (d, J = 4.8 Hz, 1H), 1.32 (s, 9H). C NMR (100 MHz, CDCl3) δ 155.1, 140.5, 129.1, 128.9, 128.4, 128.3, 127.5, 127.5, 119.3, 116.5, 60.2, 56.3, 22.8. (S)-N-((R)-(2-Methoxyphenyl) (phenyl)methyl)-2methylpropane-2-sulfinamide (7k). A colorless oil (38.9 mg, 49%). H NMR (400 MHz, CDCl3) δ 6.73−7.43 (m, 9H), 5.81 (d, J = 4.4 Hz, 1H), 5.20 (d, J = 4.4 Hz, 1H), 1.32 (s, 9H). C NMR (100 MHz, CDCl3) δ 156.6, 141.2, 130.8, 128.9, 128.5, 128.2, 128.0, 128.0, 127.5, 127.3, 57.4, 55.9, 55.5, 22.7. (S)-2-Methyl-N-((R)-1-(pyridin-2-yl)ethyl)propane-2sulfinamide (7l). A colorless oil (49.2 mg, 74%). H NMR (400 MHz, CDCl3) δ 8.60 (d, J = 4.8 Hz, 1H), δ 7.68 (m, 1H), 7.30 (m, 1H), 7.19 (m, 1H), 4.85 (d, J = 4.4 Hz, 1H), 4.64 (m, 1H), 1.52 (d, J = 6.8 Hz, 3H), 1.27 (s, 9H). C NMR (100 MHz, CDCl3) δ 161.9, 149.0, 136.8, 122.3, 121.0, 55.6, 55.2, 23.4, 22.7. (S)-N-((R)-1-(Furan-2-yl)ethyl)-2-methylpropane-2-sulfinamide (7m). A colorless oil (48.4 mg, 90%). H NMR (400 MHz, CDCl3) δ 7.38 (t, J = 3.6 Hz, 1H), 6.27−6.34 (m, 2H), 4.59 (m, 1H), 3.59 (d, J = 4.0 Hz, 1H), 1.62 (d, J = 6.8 Hz, 3H), 1.23 (s, 9H). C NMR (100 MHz, CDCl3) δ 156.0, 142.0, 110.2, 106.1, 55.7, 48.6, 22.5, 20.2. HRMS (ESI-TOF) m/z: [M + H] calcd for C10H17NO2S 216.1053, found 216.1059. (S)-N-((S)-2-Chloro-1-(4-chlorophenyl)ethyl)-2-methylpropane-2-sulfinamide (7n). A colorless oil (66.2 mg, 90%). H NMR (400 MHz, CDCl3) δ 7.28−7.38 (m, 4H), 4.68 (m, 1H), 3.87 (d, J = 5.6 Hz, 2H), 3.84 (s, 1H), 1.25 (s, 9H).