Issue 18, 2012

C2-symmetric proline-derived tetraamine as highly effective catalyst for direct asymmetric Michael addition of ketones to chalcones

Abstract

A C2-symmetric tetraamine catalyst was developed for the asymmetric Michael addition of ketones to chalcones. The corresponding adducts 1,5-dicarbonyl compounds were obtained in good chemical yields with high levels of diastereo- and enantioselectivities (up to >99 : 1 dr and 93% ee) under mild conditions. By studying the ESI-MS of the intermediates, a proposed mechanism was disclosed.

Graphical abstract: C 2-symmetric proline-derived tetraamine as highly effective catalyst for direct asymmetric Michael addition of ketones to chalcones

Supplementary files

Article information

Article type
Paper
Submitted
10 Nov 2011
Accepted
25 Jan 2012
First published
25 Jan 2012

Org. Biomol. Chem., 2012,10, 3721-3729

C 2-symmetric proline-derived tetraamine as highly effective catalyst for direct asymmetric Michael addition of ketones to chalcones

S. Ma, L. Wu, M. Liu and Y. Wang, Org. Biomol. Chem., 2012, 10, 3721 DOI: 10.1039/C2OB06897D

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