Synfacts 2008(8): 0880-0880  
DOI: 10.1055/s-2008-1078546
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

a-(N,N-Diacylamino)acroleins in Asymmetric Diels-Alder Reactions

Contributor(s): Benjamin List, Steffen Müller
K. Ishihara*, K. Nakano, M. Akakura
Nagoya University, and Aichi University of Education, Japan
Further Information

Publication History

Publication Date:
23 July 2008 (online)

Significance

An enantioselective Diels-Alder reaction of different dienes 1 and phthalimido­acrolein 2, catalyzed by chiral ammonium salts, is reported. The combination of chiral triamine 3 and pentafluorobenzenesulfonic acid showed high catalytic activity and enantioselectivity. Thus the Diels-Alder products were obtained in 52-91% yield and enantioselectivities up to er = 98:2. Additionally, theoretical studies on plausible transition states were conducted as well.