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Synfacts 2008(12): 1329-1329  
DOI: 10.1055/s-0028-1083574
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

A New Catalyst for the Desymmetrization of Cyclic Anhydrides

Contributor(s): Benjamin List, Steffen Müller
S. H. Oh, H. S. Rho, J. W. Lee, J. E. Lee, S. H. Youk, J. Chin*, C. E. Song*
University of Toronto, Canada; Sungkyunkwan University, Suwon and AmorePacific Corporation, Yongin, Korea
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Publication History

Publication Date:
20 November 2008 (online)

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Significance

A new hydrogen-bonding cinchona alkaloid based organocatalyst was designed by focusing on the prevention of catalyst self­aggregation. Due to the lack of this deactivation mode, the resulting bifunctional chiral sulfonamide 1 showed unprecedented catalytic activity in the methanolytic desymmetrization of meso-anhydrides. The reaction proceeds at room temperature within few hours in excellent yields (88-97%) and enantioselectivities (er = 95.5:4.5 to 98.5:1.5).

Review: Y. Cheng, P. McDaid, L. Deng Chem. Rev. 2003, 103, 2965-2984.