ChemInform Abstract: Enantioselective Ring‐Opening of Epoxides by HF‐Reagents. Asymmetric Synthesis of Fluoro Lactones.

Abstract

diastereoselective syntheses, enantioselective syntheses diastereoselective syntheses, enantioselective syntheses (incl. cis/trans-isomerism) O 0031 -022Enantioselective Ring-Opening of Epoxides by HF-Reagents. Asymmetric Synthesis of Fluoro Lactones.-The asymmetric ring opening of meso-(I) and racemic epoxides [cf. (III), (V)] with appropriate HF-reagents mediated by Jacobsen's enantiopure (salen)chromium chloride provides optically active fluorohydrines (up to 90% e.e.). This reaction and, more efficiently, a lipase-catalyzed deracemization are applied to synthesize enantiopure building blocks (VIII) for the preparation of both enantiomers of a fluorinated analogue of prostaglandin biosynthesis inhibitor lasiodiplodin (XII). -(HAUFE,