Journal of the American Chemical Society, Vol.133, No.13, 4694-4697, 2011
N-Heterocyclic Carbene-Catalyzed (4+2) Cycloaddition/Decarboxylation of Silyl Dienol Ethers with alpha,beta-Unsaturated Acid Fluorides
Herein we report the first all-carbon N-heterocyclic carbene-catalyzed (4 + 2) cycloaddition. The reaction proceeds with alpha,beta-unsaturated acid fluorides and silyl dienol ethers and produces 1,3-cyclohexadienes with complete diastereocontrol (dr > 20:1) while demonstrating a new type of reaction cascade exploiting alpha,beta-unsaturated acyl azoliums.