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

Masato Ito; Sachiko Kitahara; Takao Ikariya

doi:10.1021/ja050770g

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 journal › Article › peer-review

181 Citations (Scopus)

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.

Original language	English
Pages (from-to)	6172-6173
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	17
DOIs	https://doi.org/10.1021/ja050770g
Publication status	Published - May 4 2005
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja050770g

Cite this

@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 = may,

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

C2 - 15853313

AN - SCOPUS:18244394041

SN - 0002-7863

VL - 127

SP - 6172

EP - 6173

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 17

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this