title: CpRu(PN) complex-catalyzed isomerization of allylic alcohols and its application to the asymmetric synthesis of muscone.
abstract: Highly efficient isomerization of allylic alcohols into saturated carbonyls is accomplished using the catalyst system of Cp*RuCl[Ph2P(CH2)2NH2-kappa2-P,N]-KOt-Bu (Cp* = eta5-C5(CH3)5) under mild conditions. Mechanistic consideration based on isotope-labeling experiments indicated the present reaction is applicable to the asymmetric isomerization of racemic sec-allylic alcohols with a prochiral olefin via dynamic kinetic resolution. A concise asymmetric synthesis of muscone has been achieved, where the asymmetric isomerization using an optically active ligand is a key reaction.
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering and Frontier Collaborative Research Center, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan.
authors.forename: Masato
authors.initials: M
authors.lastname: Ito
authors.forename: Sachiko
authors.initials: S
authors.lastname: Kitahara
authors.forename: Takao
authors.initials: T
authors.lastname: Ikariya
mesh_terms: D002384:Catalysis; D003516:Cycloparaffins / Q000138:chemical synthesis*; D007536:Isomerism; D009942:Organometallic Compounds / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry
chemical_list: D003516:Cycloparaffins; D009942:Organometallic Compounds; D020005:Propanols; C006463:allyl alcohol; D012428:Ruthenium; C031021:muscone