Tetrahedron: Asymmetry

Nitrile biotransformations for the practical synthesis of highly enantiopure azido carboxylic acids and amides,'click'to functionalized chiral triazoles and chiral β-amino …

DY Ma, DX Wang, QY Zheng, MX Wang

Index: Ma, Da-You; Wang, De-Xian; Zheng, Qi-Yu; Wang, Mei-Xiang Tetrahedron Asymmetry, 2006 , vol. 17, # 16 p. 2366 - 2376

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Citation Number: 24

Abstract

Under very mild conditions, biotransformations of racemic azido nitriles using Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole-cell catalyst, afforded highly enantiopure,(R)-α-arylmethyl-and (+)-α-cyclohexylmethyl-β-azidopropanoic acids and their (S)-and (−)-carboxamide derivatives in excellent yields. The resulting functionalized chiral organoazides were converted in a straightforward fashion to a pair of ...