ChemInform Abstract: 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

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.