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Synfacts 2006(5): 0500-0500  
DOI: 10.1055/s-2006-934450
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Aza-Ene-Type Reaction

Contributor(s): Benjamin List, Sebastian Hoffmann
M. Terada*, K. Machioka, K. Sorimachi
Graduate School of Science, Tohoku University, Japan
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Publication History

Publication Date:
21 April 2006 (online)

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Significance

An organocatalyzed asymmetric aza-ene-type reaction of N-benzoylimines and ene­carbamates is described. A chiral 3,3′-disubstituted phosphoric acid allows the formation of β-aminoimine derivatives, which can be transformed to 1,3-diamines in good yields and up to 98% ee (15 examples, 0.1 mol% catalyst, r.t., 5 h).