Vinyldiazolactone as a Vinylcarbene Precursor:  Highly Selective C−H Insertion and Cyclopropanation Reactions

Vinylcarbenes are versatile synthetic intermediates, capable of asymmetric cyclopropanation and insertion into unactivated C−H bonds. The vinyldiazolactone precursor to the metal vinylcarbene possesses superior stability in comparison to previously known vinyldiazoacetates and, for the first time, a...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2006-12, Vol.128 (50), p.16038-16039
Main Authors: Bykowski, Darren, Wu, Kou-Hui, Doyle, Michael P
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Carbon - chemistry
Catalysis
Chemistry
Cyclization
Exact sciences and technology
General and physical chemistry
Hydrogen - chemistry
Lactones - chemistry
Molecular Structure
Propane - chemistry
Vinyl Compounds - chemistry
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Summary:Vinylcarbenes are versatile synthetic intermediates, capable of asymmetric cyclopropanation and insertion into unactivated C−H bonds. The vinyldiazolactone precursor to the metal vinylcarbene possesses superior stability in comparison to previously known vinyldiazoacetates and, for the first time, allows the use of Z-vinylcarbenes in asymmetric C−H insertion and cyclopropanation reactions. Dirhodium azetidinone ligated compounds are optimal catalysts. Cyclopropanation coupled with the Cope rearrangement provides access to trans-3,4-disubstituted hydroazulenes.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja066452e