2-Propenoic acid, 3-phenyl-, methyl ester → HCID 11416221, compound

Participants

Reaction Steps

In a typical experiment, a reaction flask immersed in a water bath was charged with sodium hydroxide (3.05 mmol of a commercial 1.022 N solution) and diluted with water (4.5 mL) in a dark fume hood. Part of this alkaline solution (c. 0.5 mL)4b was transferred into a vial to dissolve K2 [OsO2 (OH)4 ] (14.7 mg, 0.04 mmol). With vigorous stirring, n-propanol (4 mL) and benzyl carbamate (0.469 g, 3.1 mmol) were added to the flask, followed by dropwise addition of freshly prepared t-butyl hypochlorite (0.331 g, 0.346 mL, 3.05 mmol). After five minutes, an n-propanol solution (3.5 mL) of (DHQD)2AQN (34.3 mg, 0.04 mmol) (Aldrich cat. no.: 45,671-3) and methyl cinnamate (0.162 g, 1 mmol), and the aqueous K2 [OsO2 (OH)4 ] solution were added. After 1.5 h, the solution was quenched with 0.5 g sodium bisulfite. After the usual workup (Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2813-2817), 0.206 g (62% yield, 92% ee) of the pure (2S,3R)-N-benzyloxycarbonyl-3-phenylserine methyl ester (B, entry 1, R=H) was isolated via chromatography on silica gel (hexane/EtOAc=5:1, A elutes before B).

Provenance & Evidence