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

摘要

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 [l,3]-chirality transfer through the [3.3] sigmatropic rearrangement of allyl cy-anates.Stereocontrolled syntheses of lentiginosine (1) and polyoxamic acid derivative 2 from a common intermediate 7 derived from D-tartaric acid (8),have been accomplished.