Journal of Organic Chemistry 2008-11-07

Kinetic resolution of racemic alcohols using thioamide modified 1-methyl-histidine methyl ester.

Xue-Li Geng, Jia Wang, Guo-Xing Li, Peng Chen, Shu-Fang Tian, Jin Qu

Index: J. Org. Chem. 73(21) , 8558-62, (2008)

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Abstract

The low-molecular-weight and easily prepared N-thiobenzoyl 1-methyl-histidine methyl ester 3k was utilized to efficiently catalyze the kinetic resolution of racemic secondary alcohols. Comparison of the conformations of amide catalyst 3c and thioamide catalyst 3k was made to understand the origin of the improvement of the enantioselectivity by thioamide modification.