Journal of Sulfur Chemistry 655
114.2, 124.9, 129.2, 129.3, 130.1, 130.8, 133.6, 158.9, 169.8, 197.4. MS (m/z): 330 (M+ (3)),
221 (85), 193 (100), 161 (30), 152 (28), 121 (82), 101 (23), 91 (10), 77 (12), 65 (12), 43 (60).
4.2.4. 3-(4-Fluorophenyl)-2-oxo-1-(phenylthio)propyl acetate ( 2d)
1
Yellow oil. IR (neat): 3062, 2926, 1737, 1511, 1226 cm−1. H NMR (400 MHz, CDCl3) δ:
2.18 (s, 3H), 3.85 (q, J = 16.0 Hz, 2H), 6.27 (s, 1H), 6.95–7.00 (m, 2H), 7.07–7.10 (m, 2H),
7.32–7.35 (m, 3H), 7.46–7.48 (m, 2H) 13C NMR (100 MHz, CDCl3) δ: 20.7, 44.7, 81.2, 115.3,
115.5, 128.5, 129.2, 129.3, 129.8, 131.2, 131.3, 133.5, 163.3, 169.8, 196.8. MS (m/z): 209
(M+−109 (49)), 181 (44), 149 (2), 110 (42), 101 (4), 83 (6), 65 (8), 43 (100), 39 (3).
4.2.5. 2-Oxo-1-(phenylthio)-3-(4-(trifluoromethyl)phenyl)propyl acetate ( 2e)
Yellow oil. IR (neat): 3066, 2922, 1754, 1729, 1328 cm−1. 1H NMR (400 MHz, CDCl3) δ: 2.19
(s, 3H), 3.93 (ABq, J = 16.0, 44.0 Hz, 2H), 6.25 (s, 1H), 7.21 (d, J = 8.0 Hz, 2H), 7.29–7.35
(m, 3H), 7.44 (d, J = 8.0 Hz, 2H), 7.53 (d, J = 8.0 Hz, 2H). 13C NMR (100 MHz, CDCl3) δ:
20.8, 45.2, 81.5, 125.4, 125.53, 125.57, 125.6, 129.40, 129.44, 130.1, 133.6, 136.9, 169.9, 196.1.
MS (m/z): 259 (M+−109 (22)), 231 (18), 159 (11), 109 (44), 91 (5), 77 (5), 65 (15), 43 (100).
4.2.6. 3-([1,1ꢁ-Biphenyl]-4-yl)-2-oxo-1-(phenylthio)propyl acetate ( 2f)
Pale yellow oil. IR (neat): 3032, 1754, 1733, 1486, 1226 cm−1. 1H NMR (400 MHz, CDCl3) δ:
2.19 (s, 3H), 3.92 (d, J = 4.0 Hz, 2H), 6.30 (s, 1H), 7.20 (d, J = 8.0 Hz, 2H), 7.31–7.35 (m, 3H),
7.40–7.48 (m, 5H), 7.54 (dd, J = 16.0, 8.0 Hz, 4H). 13C NMR (100 MHz, CDCl3) δ: 20.9, 45.4,
81.4, 127.1, 127.42, 127.46, 128.8, 129.2, 129.4, 130.0, 130.2, 131.9, 133.6, 140.3, 140.8, 169.9,
197.0. MS (m/z): 318 (M+−58 (17)), 209 (37), 191 (5), 167 (100), 152 (26), 123 (37), 109 (10),
77 (14), 65 (10), 45 (19), 39 (6).
4.2.7. 2-Oxo-1-(phenylthio)-3-(m-tolyl)propyl acetate (2g)
Pale yellow oil. IR (neat): 3028, 2922, 1750, 1729, 1213 cm−1. 1H NMR (400 MHz, CDCl3) δ:
2.16 (s, 3H), 2.29 (s, 3H), 3.83 (s, 2H), 6.27 (s, 1H), 6.92–7.19 (m, 4H), 7.31–7.47 (m, 5H).
13C NMR (100 MHz, CDCl3) δ: 20.7, 21.3, 45.6, 81.1, 126.7, 127.9, 128.4, 129.0, 129.2, 130.4,
132.7, 133.5, 134.5, 138.1, 169.6, 197.0. MS (m/z): 254 (M+−60 (51)), 226 (7), 193 (3), 145
(7), 117 (100), 109 (28), 91 (27), 77 (19), 65 (28), 58 (15), 39 (15).
4.2.8. 2-Oxo-1-(phenylthio)-3-(o-tolyl)propyl acetate (2h)
1
Yellow oil. IR (neat): 3020, 1759, 1703, 1448, 1443, 1222 cm−1. H NMR (400 MHz, CDCl3)
δ: 2.17 (s, 6H), 3.90 (s, 2H), 6.25 (s, 1H), 7.05–7.17 (m, 4H), 7.32–7.48 (m, 5H). 13C NMR
(100 MHz, CDCl3) δ: 19.6, 20.8, 44.1, 81.4, 126.2, 127.7, 129.1, 129.2, 129.4, 130.5, 130.7,
131.7, 133.4, 137.4, 169.9, 197.0. MS (m/z): 254 (M+−60 (59)), 226 (29), 193 (9), 178 (5), 149
(86), 117 (100), 115 (98), 109 (37), 91 (40), 87 (41), 65 (43), 49 (28), 39 (24).
4.3. General procedure for the synthesis of optically active α-acyloxy thioester 3a–h
To a solution of 2a–h (0.0675 mmol) in toluene (0.5 mL) was added quinidine (2.17 mg,
0.00675 mmol), and the mixture was stirred for 8–9 h at room temperature. The crude reaction