Synfacts 2007(9): 0989-0989  
DOI: 10.1055/s-2007-968878
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

exo-Selective Diels-Alder Reaction Catalyzed by a Chiral Ammonium Salt

Contributor(s): Benjamin List, Daniela Kampen
H. Gotoh, Y. Hayashi*
Tokyo University of Science, Japan
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Publikationsverlauf

Publikationsdatum:
23. August 2007 (online)

Significance

An organocatalytic asymmetric Diels-Alder reaction is described. The ammonium salt of chiral α,α-diarylprolinol silyl ether 1 and TFA mediate the cycloaddition of aromatic as well as aliphatic α,β-unsaturated aldehydes 2 and cyclopentadiene (3) to give bicyclic products of type 4 in good yields, exo-selectivities, and enantioselectivities. Acyclic dienes 6 can also be used, which lead to the formation of optically active functionalized cyclohexenes 7.