J. Am. Chem. Soc., 127 (47), 16386 -16387, 2005. 10.1021/ja056092f S0002-7863(05)06092-0
Web Release Date: November 8, 2005

Copyright © 2005 American Chemical Society

Highly Enantioseletive Biginelli Reaction Using a New Chiral Ytterbium Catalyst: Asymmetric Synthesis of Dihydropyrimidines

Yijun Huang, Fengyue Yang, and Chengjian Zhu*

State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China, and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

cjzhu@netra.nju.edu.cn

Received September 4, 2005

Abstract:

The highly enantioselective three-component Biginelli condensation catalyzed by a recyclable chiral ytterbium triflate with a novel hexadentate amine phenol ligand containing a pyridyl group has been developed. A wide range of optically active dihydropyrimidines with remarkable pharmacological interest was obtained in high yields with good to excellent enantioselectivities under mild conditions.


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