Stereocontrolled synthesis of 3-(trans-2-aminocyclopropyl)alanine, a key component of belactosin A.

Abstract

Herein we report a concise synthesis of 3-(trans-2-aminocyclopropyl)alanine, a component of belactosin A, using asymmetric alkylation of a glycine enolate in the presence of chiral phase-transfer catalysts to control the configuration at C2. Reaction of protected glycidol with triethyl phosphonoacetate (Wadsworth-Emmons cyclopropanation) is used for enantiospecific preparation of an intermediate cyclopropanecarboxylate that is converted to a cyclopropylamine via Curtius rearrangement. [reaction: see text]

Cite this paper

@article{Armstrong2003StereocontrolledSO, title={Stereocontrolled synthesis of 3-(trans-2-aminocyclopropyl)alanine, a key component of belactosin A.}, author={Alan Armstrong and James N Scutt}, journal={Organic letters}, year={2003}, volume={5 13}, pages={2331-4} }