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Synfacts 2010(5): 0563-0563  
DOI: 10.1055/s-0029-1219671
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Oxazaborolidine-Catalyzed Diels-Alder Reaction of Maleimides

Contributor(s): Hisashi Yamamoto, Patrick Brady
S. Mukherjee, E. J. Corey*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

This combined acid system affords a general highly enantioselective Diels-Alder reaction of malemides bearing an N-benzyl, N-phenyl, or N-alkyl group. This method allows for the formation of a quaternary stereocenter, which is one of the most difficult challenges in the asymmetric Diels-Alder reaction.