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Synfacts 2008(5): 0529-0529  
DOI: 10.1055/s-2008-1072681
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Desymmetrization of Meso Anhydrides

Contributor(s): Benjamin List, Daniela Kampen
S. J. Connon*, J. Chin*, C. E. Song*
University of Dublin, Ireland, Sungkyunkwan University, Suwon and AmorePacific Corporation, Yongin, Korea; University of Toronto, Canada
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Publication History

Publication Date:
23 April 2008 (online)

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Significance

Desymmetrizations of meso anhydrides catalyzed by a cinchona alkaloid bearing a thiourea moiety are reported. Bifunctional catalyst 1 mediates the methanolysis of succinic and glutaric anhydrides 2 to give hemiesters 3 in good yields and enantioselectivities. The reactions are carried out in coordinating solvents at unusually low concentrations to prevent the dimerization or aggregation of catalyst 1 through hydrogen bonding. Its monomeric form is presumably responsible for high enantioselectivities.