Vicinal Functionalization of Propiolate Esters via Catalytic Carbocupration: Stereoselective Formation of Substituted Vinyl Silanes

The vicinal functionalization of propiolate esters via a catalytic carbocupration−silicon group migration sequence has been investigated. We have observed that catalyst loadings as low as 5 mol % allow for good yields and excellent diastereoselectivities (>20:1) with a series of Grignard reagents...

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Bibliographic Details
Published in:Organic letters 2010-06, Vol.12 (12), p.2750-2753
Main Authors: Hendrix, Amanda J. Mueller, Jennings, Michael P
Format: Article
Language:English
Subjects:
Catalysis
Combinatorial Chemistry Techniques
Copper - chemistry
Esters
Indicators and Reagents
Molecular Structure
Propionates - chemistry
Silanes - chemical synthesis
Silanes - chemistry
Stereoisomerism
Vinyl Compounds - chemical synthesis
Vinyl Compounds - chemistry
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Summary:The vicinal functionalization of propiolate esters via a catalytic carbocupration−silicon group migration sequence has been investigated. We have observed that catalyst loadings as low as 5 mol % allow for good yields and excellent diastereoselectivities (>20:1) with a series of Grignard reagents for the synthesis of substituted E-vinyl silanes.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol100854j