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Synfacts 2011(5): 0558-0558
DOI: 10.1055/s-0030-1259853
DOI: 10.1055/s-0030-1259853
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
All-Carbon [4+2] Cycloaddition Catalyzed by an NHC
S. J. Ryan, L. Candish, D. W. Lupton*
Monash University, Clayton, Australia
Further Information
Publication History
Publication Date:
15 April 2011 (online)

Significance
The first all-carbon [4+2] cycloaddition catalyzed by an N-heterocyclic carbene has been reported. A variety of α,β-unsaturated acid fluorides 2 and silyl dienol ethers 3 react to give 1,3-cyclohexadienes 4 in good to high yields with complete diastereocontrol. Mechanistic investigations support a concerted process with strong preference for endo orientation of the coupling partners. Use of cyclic dienolates proved crucial for the success of the reaction as acyclic or aldehyde-derived dienolates delivered O-acylation products.