Intramolecular Hydrogen Transfer Reaction: Menthon from Isopulegol

The flavor menthon (isomeric mixture of (−)-menthon and (+)-isomenthon) was obtained in good yields and selectivities by a solventless ruthenium catalyzed isomerization of the homoallylic alcohol (−)-isopulegol. In contrast to most previous assumptions on such “isomerization” reactions, this reactio...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 16; no. 10; pp. 2575 - 2577
Main Authors Schaub, Thomas, Rüdenauer, Stefan, Weis, Martine
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.05.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
IRON PENTACARBONYL
MECHANISM
ALLYLIC ALCOHOLS
UNSATURATED ALCOHOLS
STEREOCHEMISTRY
COMPLEXES
CARBONYL-COMPOUNDS
OLEFIN ISOMERIZATION
SATURATED KETONES
Online AccessGet full text

Cover

More Information
Summary:The flavor menthon (isomeric mixture of (−)-menthon and (+)-isomenthon) was obtained in good yields and selectivities by a solventless ruthenium catalyzed isomerization of the homoallylic alcohol (−)-isopulegol. In contrast to most previous assumptions on such “isomerization” reactions, this reaction follows an intermolecular pathway, with menthol and pulegon being the central intermediates in this transformation.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500811u