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

Org Biomol Chem

Department of Chemistry, The Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, China.

Published: May 2012

A C(2)-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.

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http://dx.doi.org/10.1039/c2ob06897dDOI Listing

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