High Substrate/Catalyst Organocatalysis by a Chiral Brønsted Acid for an Enantioselective Aza-Ene-Type Reaction
Masahiro Terada*, Kyoko Machioka, Keiichi Sorimachi
*Department of Chemistry, Graduate School of Science, Tohoku University,
Aramaki, Aoba-ku, Sendai 980-8578, Japan, Email: mterada
mail.tains.tohoku.ac.jp
M. Terada, K. Machioka, K. Sorimachi, Angew. Chem. Int. Ed., 2006, 45, 2254-2257.
DOI: 10.1002/anie.200503477
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Abstract
A highly efficient enantioselective aza-ene-type reaction of N-benzoylimines with enecarbamates has been developed. The reaction can be performed at extremely low loading of a chiral Brønsted acid catalyst without notable loss in enantioselectivity.
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proposed mechanism
Key Words
asymmetric synthesis, Brønsted acids, ene reaction, organocatalysis, phosphoric acid, β-amino ketones
ID: J06-Y2006-900
