Stereoselective Synthesis of Tri- and Tetrasubstituted Alkenes by Iron-Catalyzed Carbometalation Ring-Opening Reactions of Cyclopropenes

Open sesame: An iron‐catalyzed cyclopropene carbometalation ring‐opening sequence using trialkylaluminum reagents is described. The reactions proceed with high levels of regio‐ and stereocontrol to provide a range of multisubstituted alkenes, including trisubstituted vinylsilanes, trisubstituted vin...

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Published inAngewandte Chemie (International ed.) Vol. 47; no. 38; pp. 7350 - 7353
Main Authors Wang, Yi, Fordyce, Euan A.F, Chen, Fung Yan, Lam, Hon Wai
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 08.09.2008
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
alkenes
Alkenes - chemical synthesis
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclopropanes - chemistry
iron
Iron - chemistry
nucleophilic addition
Physical Sciences
Science & Technology
small ring systems
Stereoisomerism
strained molecules
strained molecules
ASYMMETRIC-SYNTHESIS
CRYSTAL-STRUCTURE
ALLYLINDATION
alkenes
ALKYNES
CARBOMETALLATION
COUPLING REACTIONS
small ring systems
ARYLMAGNESIATION
CONSTRUCTION
iron
nucleophilic addition
DERIVATIVES
GRIGNARD-REAGENTS
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Summary:Open sesame: An iron‐catalyzed cyclopropene carbometalation ring‐opening sequence using trialkylaluminum reagents is described. The reactions proceed with high levels of regio‐ and stereocontrol to provide a range of multisubstituted alkenes, including trisubstituted vinylsilanes, trisubstituted vinylstannanes, and all‐carbon tetrasubstituted alkenes.
Bibliography:http://dx.doi.org/10.1002/anie.200802391
istex:02C18B89A621497F2B25F9424AB77F6800238575
This work was supported by EaStCHEM (The Edinburgh and St. Andrews Research School of Chemistry) and Hoffmann-La Roche. The EPSRC National Mass Spectrometry Service Centre at the University of Wales, Swansea is thanked for providing high resolution mass spectra.
EaStCHEM
Hoffmann-La Roche
ark:/67375/WNG-K3K37Q0L-Z
ArticleID:ANIE200802391
This work was supported by EaStCHEM (The Edinburgh and St. Andrews Research School of Chemistry) and Hoffmann‐La Roche. The EPSRC National Mass Spectrometry Service Centre at the University of Wales, Swansea is thanked for providing high resolution mass spectra.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200802391