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Synfacts 2010(2): 0234-0234  
DOI: 10.1055/s-0029-1219137
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Alcoholysis of σ-Symmetric Cyclic Dicarboxylic Anhydrides

Contributor(s): Benjamin List, Kristina Zumbansen
T. Honjo, T. Tsumura, S. Sano*, Y. Nagao, K. Yamaguchi, Y. Sei
University of Tokushima and Tokushima Bunri University, Kagawa, Japan
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Publication History

Publication Date:
21 January 2010 (online)

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Significance

An enantioselective alcoholysis of σ-symmetric dicarboxylic anhydrides with benzyl alcohol catalyzed by sulfonamide 1, which was readily synthesized from (1R,2R)-N,N-dimethyl-1,2-diphenyl-1,2-ethanediamine, is reported. Mono-, bi- and tricyclic dicarboxylic anhydrides afforded the corresponding methyl esters in good to high yields and enantioselectivities. Remarkably, the hydrolysis of tricyclic anhydrides is not accessible using enzymes. Moreover, a plausible dual activation of anhydride and benzyl alcohol is proposed based on cold-spray ionization mass spectrometry studies.