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Synfacts 2006(4): 0394-0394  
DOI: 10.1055/s-2006-932103
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Aza-Diels-Alder Reaction Catalyzed by a Chiral Brønsted Acid

Contributor(s): Benjamin List, Subhas Chandra Pan
Y. Tamura, J. Itoh, H. Morita, K. Fuchibe, T. Akiyama*
Gakushunin University, Tokyo, Japan
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

Here the authors report an enantio­selective aza-Diels-Alder reaction of Danishefsky’s diene with aldimines using a phosphoric acid catalyst. The authors have observed improved enantioselectivities by using acetic acid as an ­additive. With 5 mol% of catalyst 1, good yields (72-100%) and high enantioselectivities (76-91%) are obtained for different aromatic ­aldimines.