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:
hayashi
ci.kagu.tus.ac.jp
Y. Hayashi, S. Samanta, H. Gotoh, H. Ishikawa, Angew. Chem. Int. Ed., 2008, 47, 6634-6637.
DOI: 10.1002/ange.200801408
Abstract
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
