4.8 Article

Enantioselective N-Heterocyclic Carbene Catalysis via Acyl Azolium without Exogenous Oxidants

Journal

ACS CATALYSIS
Volume 10, Issue 20, Pages 11791-11796

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c02705

Keywords

enantioselective catalysis; N-heterocyclic carbene; alpha,beta-unsaturated acyl azolium; (3+3)-annulation; (3+2)-annulation; (4+2) annulation

Funding

  1. Australian Research Council [DP1701013567]

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An approach to the alpha,beta-unsaturated acyl azolium has been developed that exploits N-heterocyclic carbenes (NHCs) and acyl fluorides, without additional oxidants, bases, or preactivated pro-nucleophiles. These conditions have been applied in four classes of NHC-catalyzed reaction. In all cases, the expected products were produced with high yield and enantioselectivity, using two sets of closely related reaction conditions, without additional optimization.

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