Rhodium(II)-Catalyzed Stereoselective Synthesis of Allylsilanes

The rhodium-catalyzed decomposition of 2-(triisopropylsilyl)ethyl aryl- and vinyldiazoacetates results in the stereoselective formation of Z-allylsilanes. The transformation is considered to proceed by silyl-directed intramolecular C–H functionalization to form a β-lactone intermediate followed by a...

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Bibliographic Details
Published in:Organic letters 2013-12, Vol.15 (24), p.6120-6123
Main Authors: Guptill, David M, Cohen, Carolyn M, Davies, Huw M. L
Format: Article
Language:English
Subjects:
Catalysis
Molecular Structure
Organometallic Compounds - chemistry
Rhodium - chemistry
Silanes - chemical synthesis
Silanes - chemistry
Stereoisomerism
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Summary:The rhodium-catalyzed decomposition of 2-(triisopropylsilyl)ethyl aryl- and vinyldiazoacetates results in the stereoselective formation of Z-allylsilanes. The transformation is considered to proceed by silyl-directed intramolecular C–H functionalization to form a β-lactone intermediate followed by a silyl-activated extrusion of carbon dioxide.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4028978