反应详情

Tetrahydrofuran (60 mL) was added to chirally-enriched N,N-bis(2-oxiranylmethyl)benzenesulfonamide (from step (i) above; 14.8 g, 55 mmol), followed by dilute sulfuric acid (15 mL of 1 M), and the mixture stirred for 3 days. Solid sodium chloride (11 g) was added and the mixture stirred for 1 hour. The organic phase was separated and concentrated under reduced pressure to give crude product (22.4 g). The material was purified by column chromatography over silica, eluting with dichloromethane:ethanol (19:1), to give the title compound (4 g, 25%) and an impure fraction that was a 2:1 mixture of cis- and trans-isomers (8 g, 75%).

1. stirringthe mixture stirred for 1 hour
2. customThe organic phase was separated
3. concentrationconcentrated under reduced pressure
4. customto give crude product (22.4 g)
5. customThe material was purified by column chromatography over silica
6. washeluting with dichloromethane:ethanol (19:1)