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Synfacts 2007(11): 1204-1204  
DOI: 10.1055/s-2007-991239
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective 1,3-Dipolar Cycloaddition of Enones and Azomethine Imines

Contributor(s): Benjamin List, Subhas Chandra Pan
W. Chen, W. Du, Y.-Z. Duan, Y. Wu, S.-Y. Yang, Y.-C. Chen*
Sichuan University, Chengdu, P. R. of China
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Publication History

Publication Date:
23 October 2007 (online)

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Significance

Here the authors report an organocatalytic asymmetric 1,3-dipolar cycloaddition between cyclic enones and azomethine imines. Cinchona alkaloid derived bifunctional primary amine catalyst 1 in combination with 2,4,6-triisopropylbenzene sulfonic acid (TIPBA) acts as an efficient catalyst system for this reaction. The authors have observed a strong counteranion effect on the rate of the reaction. With 10 mol% of catalyst 1 good to excellent yields (67-99%) and excellent enan­tioselectivities (er = 93:7 to 97:3) are obtained for different azomethine imines.