Asymmetric Reduction of Fluorinated Ketones and Keto Esters with Baker's Yeast

Abstract

Reduction of fluorinated ketones and keto esters with baker's yeast was studied. The mono(perfluoroalkyl) ketones and keto esters were asymmetrically reduced to give the corresponding optically active alcohols and hydroxy esters. Bis(perfluoroalkyl) ketones were, however, strongly resistant to the action of the baker's yeast and none of alcohols were obtained (Tables 1 and 2). Furthermore, a variety of highly diastereoselective reductions of a-monofluoro-8keto esters and 2-fluoro-1-phenyl-1-propanone were performed.