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

Hiroaki Gotoh and Yujiro Hayashi*

*Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Email: hayashici.kagu.tus.ac.jp

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

DOI: 10.1021/ol071009+ (free Supporting Information)


Abstract

2-[bis(3,5-bis-trifluoromethylphenyl) triethylsiloxymethyl]pyrrolidine is an effective organocatalyst of an exo-selective, enantioselective Diels-Alder reaction of α,β-unsaturated aldehydes in the presence of CF3CO2H.

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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

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


Key Words

Diels-Alder Reaction, Organocatalysis


ID: J54-Y2007-2410