Highly Efficient, Facile, Room Temperature Intermolecular [5 + 2] Cycloadditions Catalyzed by Cationic Rhodium(I): One Step to Cycloheptenes and Their Libraries

A cationic rhodium(I) complex―[(C10H8)Rh(cod)]+ SbF6 −―catalyzes the remarkably efficient intermolecular [5 + 2] cycloaddition of vinylcyclopropanes (VCPs) and various alkynes, providing cycloheptene cycloadducts in excellent yields in minutes at room temperature. The efficacy and selectivity of thi...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 7; pp. 1604 - 1607
Main Authors Wender, Paul A, Sirois, Lauren E, Stemmler, René T, Williams, Travis J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.04.2010
Amer Chemical Soc
Subjects
Catalysis
Cations - chemistry
Chemistry
Chemistry, Organic
Cyclization
Cycloheptanes - chemical synthesis
Cycloheptanes - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Physical Sciences
Rhodium - chemistry
Science & Technology
Small Molecule Libraries
Stereoisomerism
Temperature
7-MEMBERED RINGS
DIELS-ALDER REACTION
COMPLEXES
VINYLCYCLOPROPANES
METAL
POLYCYCLIC COMPOUNDS
ALLENES
ASYMMETRIC TOTAL-SYNTHESIS
INTRAMOLECULAR 4+2
CYCLOISOMERIZATION REACTIONS
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Summary:A cationic rhodium(I) complex―[(C10H8)Rh(cod)]+ SbF6 −―catalyzes the remarkably efficient intermolecular [5 + 2] cycloaddition of vinylcyclopropanes (VCPs) and various alkynes, providing cycloheptene cycloadducts in excellent yields in minutes at room temperature. The efficacy and selectivity of this catalyst are also shown in a novel diversification strategy, affording a cycloadduct library in one step from nine commercially available components.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol100337m