Single-Isomer Tetrasubstituted Olefins from Regioselective and Stereospecific Palladium-Catalyzed Coupling of β-Chloro-α-iodo-α,β-unsaturated Esters

The efficient regioselective and stereospecific synthesis of tetrasubstituted olefins using a mild and convenient method is disclosed. 2-Alkynyl esters are selectively converted to E-β-chloro-α-iodo-α,β-unsaturated esters by exposure to Bu4NI in refluxing dichloroethane. These products are produced...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-04, Vol.71 (9), p.3615-3618
Main Authors: Lemay, Alison B, Vulic, Katarina S, Ogilvie, William W
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Catalysis
Chemistry
Esters
Exact sciences and technology
Hydrocarbons, Chlorinated - chemistry
Hydrocarbons, Iodinated - chemistry
Organic chemistry
Palladium - chemistry
Stereoisomerism
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Summary:The efficient regioselective and stereospecific synthesis of tetrasubstituted olefins using a mild and convenient method is disclosed. 2-Alkynyl esters are selectively converted to E-β-chloro-α-iodo-α,β-unsaturated esters by exposure to Bu4NI in refluxing dichloroethane. These products are produced cleanly, regio- and stereoselectively, and in high yields. Single-isomer tetrasubstituted olefins bearing four different carbon substituents are then synthesized by sequential palladium-catalyzed coupling reactions. Selectivity results from reactivity differences in the intermediate substrates.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo060144h