1,2-Amino alcohol-dependent Petasis allylboration for racemic and chiral homoallylamines

Abstract

Petasis allylboration among an aldehyde, 1,2-amino alcohol and pinacolallylboronate has been successfully accomplished at room temperature without any catalysts. A proposed reaction pathway involving the allylboration of an in situ-generated imine through a six-membered chairlike transition state is suggested to understand the role of a positioned hydroxy group and the diastereoselective outcome.