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Representative Procedure: 2-Hydroxy-1-{(1
S
*,5
R*
)-2-(4-methylbenzenesulfonyl)-2-azabicyclo[3.1.0]hex-1-yl}ethanone (10)
To a solution of ynamide 9 (136 mg, 0.486 mmol) in CH2Cl2 (5 mL) at 0 °C were successively added VO(acac)2 (6.4 mg, 0.024 mmol, 0.05 equiv) and TBHP (0.220 mL, 5.5M in decane, 1.21 mmol, 2.5
equiv). After 0.5 h at r.t., the reaction mixture was cooled to 0 °C and cautiously
hydrolyzed with a 25% aqueous solution of Na2S2O3. After extraction with CH2Cl2, the combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified
by flash chromatography (PE-EtOAc, 55:45) to afford 52 mg (40%) of 10 as a colorless oil. IR: 3475, 1701, 1339, 1160, 1086, 903, 808, 666 cm-1. 1H NMR (300 MHz, CDCl3): δ = 7.70 (d, J = 8.5 Hz, 2 H), 7.34 (d, J = 8.5 Hz, 2 H), 5.24 (d, AB syst, J = 19.1 Hz, 1 H), 4.56 (d, AB syst, J = 19.1 Hz, 1 H), 3.70 (ddd, J = 10.6, 9.0, 2.5 Hz, 1 H), 3.03 (br s, 1 H, OH), 2.81 (ddd, app td, J = 10.6, 9.5 Hz, 1 H), 2.45 (s, 3 H), 2.27-2.15 (m, 1 H), 1.92-1.83 (m, 3 H), 0.62
(dd, app t, J = 4.5 Hz, 1 H). 13C NMR (75 MHz, CDCl3): δ = 206.3 (s), 144.8 (s), 131.9 (s), 129.7 (d, 2 C), 128.9 (d, 2 C), 67.1 (t),
53.9 (s), 49.6 (t), 34.2 (d), 25.8 (t), 21.6 (q), 16.8 (t). MS (EI, 70 eV): m/z (%) = 295 (4)[M+], 293 (7), 264 (9), 155 (15), 141 (10), 140 (100), 139 (11), 92 (19), 91 (82), 89
(8), 82 (74), 80 (8), 65 (29), 55 (86), 54 (11), 53 (10). Anal. Calcd for C14H17NO4S: C, 56.93; H, 5.80; N, 4.74. Found: C, 56.88; H, 5.93; N, 4.61.
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