Formic Acid → (2S,3S)-3-benzyloxycarbonylamino-1-chloro-2-hydroxy-4-naphthylbutane

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Reaction Steps

(3S)-3-Benzyloxycarbonylamino-1-chloro-4-naphthyl-2-butanone (190.1 mg, 0.5 mmol) and a formic acid/triethylamnine azeotropic mixture (0.1 ml) were added to a solution of chloro(pentamethylcyclopentadienyl)rhodium (III) (1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (0.34 mg, 0.0005 mmol, s/c=1000) in ethyl acetate (0.5 ml), followed by stirring at room temperature for 2 hours. After completion of the reaction, purification by silica gel column chromatography gave a desired compound, (2S,3S)-3-benzyloxycarbonylamino-1-chloro-2-hydroxy-4-naphthylbutane (179.0 mg; yield: 93.3%). As a result of HPLC analysis, the production ratio of the desired (2S,3S)-form to the isomeric (2R,3S)-form, (2S,3S):(2R,3S), was 10.9:1. The results of elementary analysis were as follows.

Provenance & Evidence