Propargyl Alcohols as β-Oxocarbenoid Precursors for the Ruthenium-Catalyzed Cyclopropanation of Unactivated Olefins by Redox Isomerization

An atom-economical method for the direct synthesis of [3.1.0]- and [4.1.0]-bicyclic frameworks via Ru-catalyzed redox bicycloisomerization of enynols is reported. The presented results highlight the unique reactivity profile of propargyl alcohols, which function as β-oxocarbene precursors, in the pr...

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Published inJournal of the American Chemical Society Vol. 133; no. 13; pp. 4766 - 4769
Main Authors Trost, Barry M, Breder, Alexander, O’Keefe, B. Michael, Rao, Meera, Franz, Adam W
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.04.2011
Amer Chemical Soc
Subjects
Alkenes - chemistry
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclization
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Oxidation-Reduction
Physical Sciences
Propanols - chemistry
Ruthenium - chemistry
Science & Technology
Stereoisomerism
ORGANIC-SYNTHESIS
ACTIVATION
CARBONATES
CHROMIUM CARBENE COMPLEXES
FACILE CONSTRUCTION
ESTERS
CYCLOISOMERIZATION
SKELETONS
CYCLIZATION
ENYNES
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Summary:An atom-economical method for the direct synthesis of [3.1.0]- and [4.1.0]-bicyclic frameworks via Ru-catalyzed redox bicycloisomerization of enynols is reported. The presented results highlight the unique reactivity profile of propargyl alcohols, which function as β-oxocarbene precursors, in the presence of a ruthenium(II) complex. Furthermore, a rare case of a formal vinylic C−H insertion reaction is described.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja200971v