Indium Mediated Reformatsky-Type Allylation of N- tert-Butanesulfinyl Iminoester with 1,3-Butadiene

Org Lett. 2024 Dec 20. doi: 10.1021/acs.orglett.4c04086. Online ahead of print.

Abstract

This study presents the indium-mediated three-component radical Reformatsky-type allylation of N-tert-butanesulfinyl iminoester with 1,3-butadiene. This novel approach offers a rapid synthesis pathway to valuable homoallylic noncanonical amino acids, demonstrated with over 30 examples showing nice regio- and diastereoselectivity. Mechanism studies revealed that allylindium complexes served as key intermediates, formed through a single-electron reduction of allylic radicals by Indium species.