Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes

Changhe Zhang; David W. Lupton

doi:10.1021/acs.orglett.7b01981

Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes

Changhe Zhang, David W. Lupton

School of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

19 Citations (Scopus)

Abstract

An enantioselective NHC (N-heterocyclic carbene) catalyzed synthesis of indenes from bifunctional α,β-unsaturated acyl fluorides and TMS enol ethers has been discovered. The reaction has broad generality (31 examples) and proceeds with high levels of enantioselectivity (most >92:8 er). Mechanistically the reaction likely occurs via a Michael/β-lactonization/decarboxylation sequence. Derivatization studies and limitations are discussed.

Original language	English
Pages (from-to)	4456-4459
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.7b01981
Publication status	Published - 1 Sep 2017

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AB - An enantioselective NHC (N-heterocyclic carbene) catalyzed synthesis of indenes from bifunctional α,β-unsaturated acyl fluorides and TMS enol ethers has been discovered. The reaction has broad generality (31 examples) and proceeds with high levels of enantioselectivity (most >92:8 er). Mechanistically the reaction likely occurs via a Michael/β-lactonization/decarboxylation sequence. Derivatization studies and limitations are discussed.

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Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes

Abstract

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