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Asymmetric Diels-Alder Reactions of α,β-Unsaturated Aldehydes Catalyzed by a Diarylprolinol Silyl Ether Salt in the Presence of Water

Yujiro Hayashi*, Sampak Samanta, Hiroaki Gotoh and Hayato Ishikawa

*Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Email:

Y. Hayashi, S. Samanta, H. Gotoh, H. Ishikawa, Angew. Chem. Int. Ed., 2008, 47, 6634-6637.

DOI: 10.1002/ange.200801408 (free Supporting Information)


Enantioselective Diels-Alder reactions catalyzed by a 2-[bis(3,5-bis-trifluoromethylphenyl) trimethylsiloxymethyl]pyrrolidine salt in water provide Diels-Alder adducts with high exo selectivities and excellent enantioselectivities.

see article for more examples

Diarylprolinol Silyl Ether as Catalyst of an exo-Selective, Enantioselective Diels-Alder Reaction

H. Gotoh, Y. Hayashi, Org. Lett., 2007, 9, 2859-2862.

Key Words

Diels-Alder Reaction, Organocatalysis, Cyclohexenes, Green Chemistry

ID: J06-Y2007-2540