Cp*Ru(PN) complex-catalyzed isomerization of allylic alcohols and its application to the asymmetric synthesis of muscone

Masato Ito, Sachiko Kitahara, Takao Ikariya

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172 Citations (Scopus)

Abstract

Highly efficient isomerization of allylic alcohols into saturated carbonyls is accomplished using the catalyst system of Cp*RuCl[Ph2P(CH2)2NH22-P,N]-KOt-Bu (Cp* = η5-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.

Original languageEnglish
Pages (from-to)6172-6173
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number17
DOIs
Publication statusPublished - May 4 2005
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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