CpRu(PN) complex-catalyzed isomerization of allylic alcohols and its application to the asymmetric synthesis of muscone.
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.
Ito
Masato
M
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.
Kitahara
Sachiko
S
Ikariya
Takao
T
D002384:Catalysis; D003516:Cycloparaffins / Q000138:chemical synthesis*; D007536:Isomerism; D009942:Organometallic Compounds / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry
D003516:Cycloparaffins; D009942:Organometallic Compounds; D020005:Propanols; C006463:allyl alcohol; D012428:Ruthenium; C031021:muscone