An Asymmetric Synthesis of a Chiral Sulfone Acid with Concomitant Hydrolysis and Oxidation to Enable the Preparation of a Glucokinase Activator

作者：DeBaillie Amy C^*; Magnus Nicholas A; Laurila Michael E; Wepsiec James P; Ruble J Craig; Petkus Jeffrey J; Vaid Radhe K; Niemeier Jeffry K; Mick Joseph F; Gunter Thomas Z

来源：Organic Process Research & Development, 2012, 16(9): 1538-1543.

DOI：10.1021/op300139g

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.

• 出版日期2012-9