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Stereoselective amination of chiral enolates: Synthesis of enantiomerically pure α,β-diamino acids, chiral key compounds in the synthesis of conformationally constrained peptido- and non-peptidomimetics

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
6
Issue
11
Identifiers
DOI: 10.1016/0957-4166(95)00368-y

Abstract

Abstract This work describes an efficient synthesis of enantiomerically pure ( R)-2-aminomethylalanine, ( R)-2-aminomethylnorvaline, ( R)-2-aminomethylvaline, ( R)-2-aminomethylleucine and ( R)-2-aminomethylphenylalanine by electrophilic amination of chiral 2-cyanoesters with O-(diphenylphosphinyl)hydroxylamine followed by appropiate reduction and hydrolysis.

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