Asymmetric synthesis takes big step forward

Abstract

Chemists at the University of Illinois, Urbana-Champaign, have devised a cheap method for catalytic asymmetric epoxidation of unsubstituted olefins [ J. Am. Chem. Soc. , 112 , 2800 (1990)]. The technique may be applied to research syntheses of natural products and industrial production of drugs, pesticides, pheromones, and flavor and fragrance additives. Such widely applicable asymmetric syntheses take on a new importance in light of the regulations concerning marketing of enantiomeric versus racemic drugs expected this spring from the Food & Drug Administration. This achievement of organic chemistry professor Eric N. Jacobsen is the latest advance in efforts to make chiral compounds from olefins. It parallels the catalytic asymmetric epoxidation of allylic alcohols and catalytic asymmetric dihydroxylation of unsubstituted olefins devised by organic chemistry professor K. Barry Sharpless at Massachusetts Institute of Technology. Like the chemistry of Sharpless, the new reaction creates two dissymmetric ca...