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Synfacts 2007(1): 0100-0100  
DOI: 10.1055/s-2006-955663
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Chiral N-Heterocyclic Carbene Catalyzed Oxodiene Diels-Alder Reactions

Contributor(s): Benjamin List, Nolwenn J. A. Martin
M. He, G. J. Uc, J. W. Bode*
University of California at Santa Barbara, USA
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Publikationsverlauf

Publikationsdatum:
15. Dezember 2006 (online)

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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.