Boc-leu-chloromethylketone → (2S,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-5-methylhexane

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Reaction Steps

(3S)-3-tert-Butoxycarbonylamino-1-chloro-5-methyl-2-hexanone (263.8 mg, 1.0 mmol) and a formic acid/triethylamine azeotropic mixture (0.2 ml) were added to a solution of chloro(pentamethylcyclopentadienyl)rhodium (III) (1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (0.67 mg, 0.0001 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, (2S,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-5-methylhexane (255.8 mg; yield: 96.4%). 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 7.7:1. The results of elementary analysis were as follows.

Provenance & Evidence