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Synfacts 2007(1): 0100-0100
DOI: 10.1055/s-2006-955663
DOI: 10.1055/s-2006-955663
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
Chiral N-Heterocyclic Carbene Catalyzed Oxodiene Diels-Alder Reactions
M. He, G. J. Uc, J. W. Bode*
University of California at Santa Barbara, USA
Further Information
Publication History
Publication Date:
15 December 2006 (online)
Significance
A highly enantioselective, chiral N-heterocyclic carbene catalyzed inverse-electron-demand 1-oxodiene Diels-Alder reaction of a wide range of enones 1, using readily available α-chloroaldehydes 2 as the dienophile precursors, is described. In the presence of chiral triazolium salt 3 as precatalyst, a variety of optically pure, functionalized dihydropyran-2-ones 4 bearing either aliphatic or aromatic substituents are obtained in good yields and with excellent enantioselectivities.