CpRu(PN) complex-catalyzed isomerization of allylic alcohols and its application to the asymmetric synthesis of muscone |
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Authors: | Ito Masato Kitahara Sachiko Ikariya Takao |
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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. |
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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. |
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