(3S)-3-Benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone → (2R, 3S)-3-benzyloxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane

Participants

Reaction Steps

(3S)-3-Benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone (331.8 mg, 1.0 mmol) and a formic acid/triethylamine azeotropic mixture (0.2 ml) were added to a solution of chloro(pentamethylcyclopentadienyl)rhodium (III) (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (0.67 mg, 0.001 mmol, s/c=1000) in ethyl acetate (1.0 ml), followed by stirring at room temperature for 2 hours. After completion of the reaction, the reaction mixture was purified by silica gel column chromatography to give a desired compound, (2R, 3S)-3-benzyloxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane (320.1 mg; yield: 95.8%). HPLC analysis revealed that the production ratio of the desired (2R,3S)-form to the isomeric (2S,3S)-form, (2R,3S):(2S,3S), was 8.5:1. The results of elementary analysis were as follows.

Provenance & Evidence