An Asymmetric Synthesis of a Chiral Sulfone Acid with Concomitant Hydrolysis and Oxidation to Enable the Preparation of a Glucokinase Activator
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- 作者：Amy C. DeBaillie ; Nicholas A. Magnus ; Michael E. Laurila ; James P. Wepsiec ; J. Craig Ruble ; Jeffrey J. Petkus ; Radhe K. Vaid ; Jeffry K. Niemeier ; Joseph F. Mick ; Thomas Z. Gunter
- 刊名：Organic Process Research & Development
- 出版年：2012
- 出版时间：September 21, 2012
- 年：2012
- 卷：16
- 期：9
- 页码：1538-1543
- 全文大小：268K
- 年卷期：v.16,no.9(September 21, 2012)
- ISSN：1520-586X
文摘
This contribution describes the demonstration of an asymmetric synthesis of a glucokinase activator via protonation of the enolate generated from an alkylaryl ketene and (R)-pantolactone. Additionally, a one-pot hydrolysis/oxidation protocol with lithium hydroperoxide was developed to afford a chiral sulfone acid without degradation of the labile stereocenter.