Domino Synthesis of -Unsaturated -Lactams via Stereo- selective Amination of -Tertiary Allylic Alcohols

Abstract

Tertiary allylic alcohols equipped with a carboxyl group can be smoothly aminated under ambient conditions via a conceptually new and stereoselective protocol under Pd catalysis. The in situ formed (Z)-configured -amino acid cyclizes to afford an ,- unsaturated -lactam releasing water as the only by-product. This practical catalytic transformation highlights the use of a carboxyl group acting as a hydrogen donor, stereodirecting and functional group to provide a wide series of pharma-relevant building blocks. Various control reactions support the crucial role of a carboxyl group in the substrate to mediate these transformations.