A novel method for a stereoselective synthesis of trisubstituted olefin using tricarbonyliron complex: a highly stereoselective synthesis of (all-E)- and (9Z)-Retinoic acids

摘要

In order to establish the stereoselective synthesis of retinoic acids, which are ligand molecules of the retinoic acid receptors (RARs, all-E-isomer) and the retinoid X receptors (RXRs, 9Z-isomer), the reaction of β-ionone-tricarbonyliron complex 7 with carbanions was investigated. Treatment of 7 with the lithium salt of acetonitrile afforded (7E,9E)-β-ionylideneacetonitroile-tricarbonyliron complex 8 exclusively, uia addition, dehydration, and migration of tricarbonyliron complex.