Stereoselective Allyl Amine Synthesis through Enantioselective Addition of Diethylzinc and [1,3]‐Chirality Transfer: Synthesis of Lentiginosine and Polyoxamic Acid Derivative

Abstract

A new synthetic method for the preparation of allyl amines has been developed. The key steps of this method are enantioselective addition of diethylzinc and [1,3]-chirality transfer through the [3.3] sigmatropic rearrangement of allyl cyanates. Stereocontrolled syntheses of lentiginosine (1) and polyoxamic acid derivative 2 from a common intermediate 7 derived from D-tartaric acid (8), have been accomplished.