Asymmetric Allenylation of Alkynes mediated by Chiral Organoselenated Reagents under Oxidative Conditions

Abstract

AbstractThe reactivity of novel chiral lactamide‐substituted diselenide‐based reagents under oxidative conditions was exploited to develop a metal‐free method for the preparation of enantioenriched allenylamides from simple alkynes in good yields, and with enantiomeric excesses up to 99 %. The key of the success in this method is attributed to the hydrogen‐bonded lactamide appendages that ensure configurational stability of chiral vinyl selenoxide intermediates for an optimal enantiotopic β‐syn‐elimination step.