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Titolo:
ZIRCONOCENE-CATALYZED CATIONIC DIELS-ALDER REACTIONS
Autore:
WIPF P; XU WJ;
Indirizzi:
UNIV PITTSBURGH,DEPT CHEM PITTSBURGH PA 15260
Titolo Testata:
Tetrahedron
fascicolo: 15, volume: 51, anno: 1995,
pagine: 4551 - 4562
SICI:
0040-4020(1995)51:15<4551:ZCDR>2.0.ZU;2-I
Fonte:
ISI
Lingua:
ENG
Soggetto:
RADICAL PERICYCLIC-REACTIONS; ALLYL CATIONS; ORGANIC-SYNTHESIS; HOMOGENEOUS CATALYSIS; CYCLO-ADDITIONS; LOW-TEMPERATURE; ORTHO-ESTERS; CYCLOPENTADIENE; CYCLOADDITIONS; PRECURSORS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
71
Recensione:
Indirizzi per estratti:
Citazione:
P. Wipf e W.J. Xu, "ZIRCONOCENE-CATALYZED CATIONIC DIELS-ALDER REACTIONS", Tetrahedron, 51(15), 1995, pp. 4551-4562

Abstract

In situ prepared Cp(2)ZrCl(+) catalyzes the formation of dioxolenium ions from alpha,beta-unsaturated epoxy esters. As a consequence of this activation process, acrylate, methacrylate and crotonate derivativesundergo a rapid and stereoselective cationic [4+2] cycloaddition witha wide range of dienes. Ring-extended carboxylic acid derivatives areformed in 1-7 h at 0-21 degrees C and in 50-90% yield after saponification of the intermediate diol esters. Simple Lewis acid catalysis by Cp(2)ZrCl(+) can be excluded on the basis of the experimental results.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 13/08/20 alle ore 14:37:55