A New Procedure for Construction of 2,6-trans-Disubstituted Piperidines Using Osmium-catalyzed Asymmetric Dihydroxylation: Application to the Synthesis of (+)-Epidihydropinidine and (+)-Solenopsin A1

Abstract

An asymmetric synthesis of (+)-epidihydropinidine (1) and (+)-solenopsin A (2) has been achieved by starting with the Sharpless asymmetric dihydroxylation of the α-amino acid-derived N-alkenylurethanes (3) followed by subsequent aminocyclization