Base-Catalyzed Stereoselective Vinylation of Ketones with Arylacetylenes: A New C(sp3)C(sp2) Bond-Forming Reaction

Autor:	Elena Yu. Schmidt, Nadezhda I. Protsuk, Nadezhda V. Zorina, Boris A. Trofimov, Elena V. Skital'tseva, Igor A. Ushakov, Al'bina I. Mikhaleva
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Base (chemistry) chemistry Stereochemistry Organic Chemistry Stereoselectivity General Chemistry Catalysis
Zdroj:	Chemistry - A European Journal. 16:8516-8521
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.201000227
Popis:	Alkylaryl- and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100 degrees C, 1 h) to give regio- and stereoselectively the (E)-beta-gamma-ethylenic ketones ((E)-3-buten-1-ones) in 61-84% yields and with approximately 100% stereoselectivity. This vinylation represents a new C(sp(3))-C(sp(2)) bond-forming reaction of high synthetic potential.
Databáze:	OpenAIRE
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