PMID: 11902867Mar 21, 2002Paper

Dynamic kinetic resolution via dual-function catalysis of modified cinchona alkaloids: asymmetric synthesis of alpha-hydroxy carboxylic acids

Journal of the American Chemical Society
L Tang, Li Deng

Abstract

A highly enantioselective catalytic transformation of racemic alpha-hydroxy acids to optically active alpha-hydroxy acids is reported. A new procedure was developed for the condensation of racemic alpha-hydroxy acids with trichloromethyl chloroformate (diphosgene) at room temperature in the presence of activated charcoal to form 5-substituted-1,3-dioxolane-2,4-diones in 90-100% yield. An efficient dynamic kinetic resolution of 5-aryl dioxolanediones was realized via a modified cinchona alkaloid-catalyzed alcoholytic opening of the dioxolanedione ring, generating a variety of optically active alpha-hydroxy esters in 91-96% ee and 61-85% chemical yield. In this dynamic kinetic resolution, the modified cinchona alkaloid was found to serve dual catalytic roles, mediating both the rapid racemization of the 5-aryl dioxolanediones and the enantioselective alcoholytic ring opening of the 5-aryl dioxolanediones. Consequently, both enantiomers of the 5-aryl dioxolanediones were converted to highly enantiomerically enriched aromatic alpha-hydroxy esters in yields (61-85%), far exceeding the maximum of 50% for a normal kinetic resolution. This development not only represents an expansion of the scope of asymmetric acyl-transfer catalysis o...Continue Reading

Citations

Jun 23, 2010·Proceedings of the National Academy of Sciences of the United States of America·Hongming LiLi Deng
Feb 28, 2006·Proceedings of the National Academy of Sciences of the United States of America·Shiue-Shien WengChien-Tien Chen
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