Asymmetric synthesis of all four stereoisomers of 1-amino-3-hydroxy-cyclopentane-1-carboxylic acid

Abstract

An asymmetric synthesis of all four stereoisomers of 1-amino-3-hydroxy-cyclopentane-1-carboxylic acid based on a chiral glycine equivalent, oxazinone derivative is presented. The crucial point of the performed reactions is the alkylation of (S)- and (R)-glycine equivalent with the respective stereoisomers of 4-(2-iodoethyl)-1,3,2-dioxathiolan-2-oxide using phosphazenic base t-BuP4.