Regiospecific ring-opening reactions of β-aziridinyl α,β-enoates with acids: application to the stereoselective synthesis of a couple of diastereoisomeric (E)-alkene dipeptide isosteres from a single β-aziridinyl α,β-enoate and to the convenient preparation of amino alcohols bearing α,β-unsaturated ester groups

Abstract

Regio- and stereo-selective ring-opening reactions of N-(2,4,6-trimethylphenylsulfonyl)-γ,δ-cis- or -trans-γ,δ-epimino (E)-α,β-enoates with acids such as methanesulfonic acid (MSA) or trifluoroacetic acid (TFA) have been found. These ring-opening reactions are useful for the stereoselective synthesis of a couple of diastereomeric (E)-alkene dipeptide isosteres from a single substrate of γ,δ-epimino (E)-α,β-enoate, and for the convenient preparation of δ-aminated γ-hydroxy α,β-enoates.