ChemInform Abstract: A New Method for the Synthesis of Cyclopentenones via the Tandem Michael Addition-Carbene Insertion Reaction of β-Ketoethynyl( phenyl)iodonium Salts

Autor:	Rik R. Tykwinski, Peter J. Stang, Bobby L. Williamson
Rok vydání:	2010
Předmět:	Cyclopentenone chemistry.chemical_compound chemistry Bicyclic molecule Silica gel Insertion reaction Stereochemistry Intramolecular force Michael reaction General Medicine Medicinal chemistry Carbene Isomerization
Zdroj:	ChemInform. 25
ISSN:	0931-7597
DOI:	10.1002/chin.199418044
Popis:	A variety of substituted 2-cyclopentenones are obtained in good yields (53-82%) via intramolecular 1,5-carbon-hydrogen insertion reactions of [β-(p-toluenesulfonyl)alkylidene]carbenes derived from Michael addition of sodium p-toluenesullanate to β-ketoethynyl(phenyl)iodonium triflates. An extension of the methodology using β-amidoethynyl(phenyl)iodonium triflates provides a facile synthesis of γ-lactams including fused bicyclic systems. The isomerization of a substituted cyclopentenone on silica gel is also reported
Databáze:	OpenAIRE
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