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

Chem Commun (Camb)

Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China.

Published: February 2025

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.

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http://dx.doi.org/10.1039/d5cc00072fDOI Listing

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