A new route to protected acyloins and their enzymatic resolution with lipases

…, U Bornscheuer, LA Wessjohann

Index: Scheid, Guenther; Kuit, Wouter; Ruijter, Eelco; Orru, Romano V. A.; Henke, Erik; Bornscheuer, Uwe; Wessjohann, Ludger A. European Journal of Organic Chemistry, 2004 , # 5 p. 1063 - 1074

Full Text: HTML

Citation Number: 21

Abstract

Abstract A series of 16 different 3-acyloxy methyl ketones, the acyloin acetates and butyrates (±)-5, was synthesised by a straightforward new method through alkylation of tert-butyl 2- acyloxyacetoacetates 3, followed by chemoselective dealkoxycarbonylation of the tert- butyloxycarbonyl group in the presence of other ester groups. Subsequent hydrolysis of (±)- 5 can be achieved with base to give racemic acyloins 6, or with lipase catalysis to afford ...