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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: mteradamail.tains.tohoku.ac.jp

M. Terada, K. Machioka, K. Sorimachi, Angew. Chem. Int. Ed., 2006, 45, 2254-2257.

DOI: 10.1002/anie.200503477 (free Supporting Information)



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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