A Highly Enantioselective Catalyst for the Asymmetric Nozaki–Hiyama–Kishi Reaction of Allylic and Vinylic Halides

Abstract

Catalytic asymmetric addition of vinylic halides and triflates to aldehydes, with useful levels of stereoinduction, has been achieved for the first time using the salen-type ligand (S,S)-5 (see scheme; PMB=para-methoxybenzyl), which contains the novel endo,endo-2,5-diamino norbornane building block. This asymmetric Nozaki–Hiyama–Kishi reaction leads to the coupling of various halides and aldehydes with high yields and enantioselectivities (up to 92 % ee).