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Enantioselective ?-Alkylation of ?,?-Unsaturated Malonates and Ketoesters by a Sequential Ir-Catalyzed Asymmetric Allylic Alkylation/Cope Rearrangement.

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

SUBMITTER: Liu WB 

PROVIDER: S-EPMC5497580 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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

Liu Wen-Bo WB   Okamoto Noriko N   Alexy Eric J EJ   Hong Allen Y AY   Tran Kristy K   Stoltz Brian M BM  

Journal of the American Chemical Society 20160418 16

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. ...[more]

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