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Synfacts 2010(4): 0482-0482  
DOI: 10.1055/s-0029-1219521
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Michael Addition Catalyzed by Chiral Bifunctional Thioureas Based on Saccharides

Contributor(s): Benjamin List, Kristina Zumbansen
H. Ma, K. Liu, F.-G. Zhang, C.-L. Zhu, J. Nie, J.-A. Ma
Tianjin University, P. R. of China
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

Ma and co-workers synthesized ­bifunctional thioureas derived from commercially available saccharides and chiral diamines. These simple catalysts proved to be efficient in the Michael-type addition of ketones to α,β-,γ,δ-nitrodienes giving perfect regioselectivity for the 1,4-addition. The corresponding products were obtained in high yields and enantioselectivities and could be easily converted into the trans- and cis-(3R)-5-substituted 3-pyrrolidine carboxylic acids.