Enantioselective formation of stereogenic carbon - Fluorine centers by a simple catalytic method

Abstract

(Chemical Equation Presented) An easy protocol has been developed for the formation of stereogenic carbon-fluorine centers by the organocatalytic asymmetric α-fluorination of aldehydes 1. The 2-fluoroaldehydes 4 are formed with 2 as the fluorinating agent and only 1 mol% of a sterically demanding silylated prolinol 3 as catalyst. The 2-fluoroaldehydes are subsequently reduced to the corresponding alcohols 5 without loss of enantiomeric excess. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.