Iridium-Catalyzed Enantioselective Allylic Substitution of Vinylcyclopropanes by Carboxylic Acids

Abstract

An efficient method for a highly regio- and enantioselective allylic substitution of vinylcyclopropanes using carboxylic acids as oxygen nucleophile via iridium catalysis has been developed. This represents a highly atom-economic approach for the synthesis of synthetically useful chiral building blocks in high yields. The practical utility of this method is demonstrated by the application of the products in useful transformations.

Catalytic Asymmetric Ring Opening Reactions of Vinylcyclopropanes

“…In this Recently, in 2023, Majumdar and co-workers disclosed a highly efficient iridium-catalyzed regio-and enantioselective allylic substitution of vinylcyclopropanes using carboxylic acids as oxygen nucleophiles (Scheme 15). [27] In presence of 2 mol% [Ir(cod)Cl] 2 and Carreira's chiral (phosphoramidite, olefin) ligand [28] L5, racemic donor-acceptor vinylcyclopropanes participate in ring-opening reactions with carboxylic acids to deliver regio-and enantioenriched allylic ester products with high yields (Scheme 15A and B). The reactions are performed under ambient conditions and the method shows wide functional group compatibility.…”