This work was partially supported by a Grant-in-Aid for Scientific Research on Priority Areas “Advanced Molecular Transformation of Carbon Resources” from the Ministry of Education, Culture, Sports, Science, and Technology (Japan). Y.Y. is grateful to the Japan Society for the Promotion of Science for Young Scientists for a research fellowship.
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Communication
A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Mannich Reactions of N-Boc-Protected Imines†
Article first published online: 28 JAN 2009
DOI: 10.1002/anie.200805628
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 48, Issue 10, pages 1838–1840, February 23, 2009
Additional Information
How to Cite
Kano, T., Yamaguchi, Y. and Maruoka, K. (2009), A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Mannich Reactions of N-Boc-Protected Imines. Angew. Chem. Int. Ed., 48: 1838–1840. doi: 10.1002/anie.200805628
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Publication History
- Issue published online: 17 FEB 2009
- Article first published online: 28 JAN 2009
- Manuscript Received: 18 NOV 2008
Funded by
- Grant-in-Aid for Scientific Research
- Ministry of Education, Culture, Sports, Science, and Technology (Japan)
- Japan Society for the Promotion of Science
Keywords:
- asymmetric catalysis;
- diastereoselectivity;
- enantioselectivity;
- Mannich reaction;
- organocatalysis
Abstract
The moderate nucleophilicity of the axially chiral amino sulfonamide (S)-1 suppresses the problematic side reactions, including aldol reactions, in the asymmetric Mannich reaction of N-Boc-protected imines with aldehydes. The corresponding adducts are obtained in good yield and excellent stereoselectivity (see scheme; Boc=tert-butoxycarbonyl, Tf=trifluoromethanesulfonyl).