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

doi:10.1055/s-2008-1078546

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Synfacts 2008(8): 0880-0880
DOI: 10.1055/s-2008-1078546

Organo- and Biocatalysis

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

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Publikationsverlauf

Publikationsdatum:
23. Juli 2008 (online)

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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.