The Stereoselective Synthesis of 2-Alkyl γ-Keto Acid and Heterocyclic Ketomethylene Peptide Isostere Core Units Using Chiral Alkylation by 2-Triflyloxy Esters

Article abstract of DOI:10.1021/jo00121a031

A simple and general protocol for the enentioselective preparation of γ-keto acids and heterocyclic γ-keto acids which have an alkyl group at C-2 is reported.The alkyl group is introduced by chiral alkylation using a scalemic 2-triflyoxy ester.The alkylation takes place with inversion of configuration and is compatible with a variety of alkyl groups.This methodology is thus wellsuited for the preparation of a wide variety of ketomethylene peptide isosteres.