Catalytic Enantioselective Allylation of Acetylenic Aldehydes by Chiral Phosphoric Acid/Transition Metal Cooperative Catalysis: Formal Synthesis of Fostriecin
Shigenobu Umemiya, Masahiro Terada
Abstract
An enantioselective allylation of silyl-substituted acetylenic aldehydes by chiral phosphoric acid (CPA)/transition metal cooperative catalysis was developed. Enantioenriched homoallylic propargyl alcohols were obtained in good yields with excellent enantioselectivities (>99% ee) under mild conditions. Moreover, the shortest formal synthesis of fostriecin was achieved by the present enantioselective allylation protocol as the key step. The known intermediate of fostriecin reported by McDonald and co-worker was synthesized in only nine steps in 39% total yield.
Topics & Concepts
Enantioselective synthesisChemistryPhosphoric acidCatalysisPropargylYield (engineering)Organic chemistryFormal synthesisTransition metalCombinatorial chemistryMetallurgyMaterials scienceAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions