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Synfacts 2010(9): 1066-1066  
DOI: 10.1055/s-0030-1257972
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Higher Enantioselectivity with Less Catalyst Loading

Contributor(s): Benjamin List, Ji-Woong Lee
H. B. Jang, H. S. Rho, J. S. Oh, E. H. Nam, S. E. Park, H. Y. Bae, C. E. Song*
Sungkyunkwan University, Suwon and AmorePacific Corporation, Yongin, South Korea
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Publication History

Publication Date:
23 August 2010 (online)

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Significance

The authors report the intrinsic problem of bifunctional organocatalysts containing acid-base functionalities in one molecule. The enantioselectivity of catalyst 3 for the desymmetrization of anhydride 1 could be increased from 55.5:45.5 er to 97.5:2.5 er by optimizing the reaction conditions. Self-association phenomenon of catalysts 3 and 7 can be prevented by installing a bulky substituent with squaramide catalyst 10. ­Also, the authors attempted to quantify the degree of self-association by DOSY NMR.