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

Masato Ito, Sachiko Kitahara, Takao Ikariya

Research output: Contribution to journalArticle

163 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

Fingerprint

Isomerization
Alcohols
Isotope Labeling
Alkenes
Ligands
Isotopes
Labeling
Olefins
Catalysts
Kinetics
muscone
allyl alcohol
Experiments

All Science Journal Classification (ASJC) codes

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

Cite this

Cp*Ru(PN) complex-catalyzed isomerization of allylic alcohols and its application to the asymmetric synthesis of muscone. / Ito, Masato; Kitahara, Sachiko; Ikariya, Takao.

In: Journal of the American Chemical Society, Vol. 127, No. 17, 04.05.2005, p. 6172-6173.

Research output: Contribution to journalArticle

@article{c9e5010da7274f2bb16b52dfaf815a35,
title = "Cp*Ru(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-κ2-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.",
author = "Masato Ito and Sachiko Kitahara and Takao Ikariya",
year = "2005",
month = "5",
day = "4",
doi = "10.1021/ja050770g",
language = "English",
volume = "127",
pages = "6172--6173",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "17",

}

TY - JOUR

T1 - Cp*Ru(PN) complex-catalyzed isomerization of allylic alcohols and its application to the asymmetric synthesis of muscone

AU - Ito, Masato

AU - Kitahara, Sachiko

AU - Ikariya, Takao

PY - 2005/5/4

Y1 - 2005/5/4

N2 - Highly efficient isomerization of allylic alcohols into saturated carbonyls is accomplished using the catalyst system of Cp*RuCl[Ph2P(CH2)2NH2-κ2-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.

AB - Highly efficient isomerization of allylic alcohols into saturated carbonyls is accomplished using the catalyst system of Cp*RuCl[Ph2P(CH2)2NH2-κ2-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.

UR - http://www.scopus.com/inward/record.url?scp=18244394041&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=18244394041&partnerID=8YFLogxK

U2 - 10.1021/ja050770g

DO - 10.1021/ja050770g

M3 - Article

VL - 127

SP - 6172

EP - 6173

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 17

ER -