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Representative Experimental Procedure: To cis-2S,2′S,3′S-N-[(3-(phenyl)-2-aziridinyl)carbonyl]bornane-10,2-sultam (4a) in a EtOAc:MeOH (1:1) mixture (5 mL) was added a substoichiometric amount of H2O, TFA and Pd(OH)2 (42 mg, 0.06 mmol). The flask was then pump filled with hydrogen and stirred at atmospheric pressure and r.t. overnight. After this time the solution was filtered through a pad of Celite®, the pad washed with further MeOH. The solvent was removed in vacuo to afford S-(5a) as a colourless solid (110 mg, 0.3 mmol, 99%); Rf = 0.46 (EtOAc); [α]D
20 +66.7 (c 1, CHCl3). IR (CCl4): νmax = 3019, 2951 (CH), 1672 (C=O), 1334, 1170 (SO2), 756, 721, 702 (Ar) cm-1. 1H NMR (250 MHz, CD3OD): δ = 1.05 and 1.20 (6 H, 2 × s), 1.28-1.50 and 1.88-2.15 (7 H, m), 2.89 (1 H, dd, J = 10.6 Hz, 14.5 Hz), 3.65 (1 H, dd, J = 2.8 Hz, 14.5 Hz), 3.76 and 3.87 (2 H, 2 × d, J = 14.2 Hz), 4.05 (1 H, dd, J = 5.0 Hz, 7.9 Hz), 4.61 (1 H, dd, J = 2.8 Hz, 10.6 Hz), 7.32-7.47 (5 H, m). 13C NMR (60 MHz, CD3OD): δ = 20.53, 21.60, 27.59, 33.95, 39.43, 37.90, 46.50, 49.70, 51.08, 53.72, 56.10, 67.26, 129.49, 130.70, 130.92, 135.92, 168.55. MS (CI): m/z (%) = 363 (33) [MH]+, 271 (22), 120 (100), 91 (13), 58 (4). Found: [MH]+, 363.1732, C19H27N2O3S requires [MH]+, 363.1743.
