Synthesis of vinyl, alkyl-substituted chiral acrylates via Krische iridium complex-catalysed allylic phosphonation

Abstract

An enantioselective preparation of vinyl, alkyl-substituted chiral α-stereogenic acrylates is reported using two consecutive steps of Ir-catalysed allylic alkylation of aliphatic allylic acetates with phosphonates and Horner–Wadsworth–Emmons olefination. Unlike commonly utilised iridium-phosphoramidite catalysts, Krische's catalyst was uniquely effective in promoting highly regio- and enantioselective reactions of alkyl-substituted allylic substrates, thus constituting a significant alternative to the known protocol.