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Enantioselective γ-Alkylation of α,β-Unsaturated Malonates and Ketoesters by a Sequential Ir-Catalyzed Asymmetric Allylic Alkylation/Cope Rearrangement

2016; American Chemical Society; Volume: 138; Issue: 16 Linguagem: Inglês

10.1021/jacs.6b02153

1943-2984

Wenbo Liu, Noriko Okamoto, Eric J. Alexy, Allen Y. Hong, Kristy Tran, Brian M. Stoltz,

Synthetic Organic Chemistry Methods

A catalytic, enantioselective γ-alkylation of α,β-unsaturated malonates and ketoesters is reported. This strategy entails a highly regio- and enantioselective iridium-catalyzed α-alkylation of an extended enolate, and a subsequent translocation of chirality to the γ-position via a Cope rearrangement.