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Titolo:
Stereoselective synthesis of chiral polyfunctionalized cyclohexane derivatives. Palladium(II)-mediated reaction between cyclohexenones and diazomethane
Autore:
Rodriguez-Garcia, C; Ibarzo, J; Alvarez-Larena, A; Branchadell, V; Oliva, A; Ortuno, RM;
Indirizzi:
Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain Univ AutonomaBarcelona Barcelona Spain E-08193 E-08193 Barcelona, Spain Univ Autonoma Barcelona, Unitat Cristallog, E-08193 Barcelona, Spain Univ Autonoma Barcelona Barcelona Spain E-08193 E-08193 Barcelona, Spain
Titolo Testata:
TETRAHEDRON
fascicolo: 6, volume: 57, anno: 2001,
pagine: 1025 - 1034
SICI:
0040-4020(20010204)57:6<1025:SSOCPC>2.0.ZU;2-0
Fonte:
ISI
Lingua:
ENG
Soggetto:
DIELS-ALDER CYCLOADDITIONS; RAY MOLECULAR-STRUCTURE; ENANTIOSELECTIVE SYNTHESIS; AMINO-ACIDS; 1,3-DIPOLAR CYCLOADDITIONS; EFFICIENT SYNTHESIS; HIGH-PRESSURE; DIENOPHILES; ANALOGS; DIENES;
Keywords:
benzoxazole; chemoselectivity; cyclohexanones; cyclohexenones; cyclopropanation; diazomethane; Diels-Alder reactions; oxiranes; palladium diacetate;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
38
Recensione:
Indirizzi per estratti:
Indirizzo: Ortuno, RM Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain Univ Autonoma Barcelona Barcelona Spain E-08193 celona, Spain
Citazione:
C. Rodriguez-Garcia et al., "Stereoselective synthesis of chiral polyfunctionalized cyclohexane derivatives. Palladium(II)-mediated reaction between cyclohexenones and diazomethane", TETRAHEDRON, 57(6), 2001, pp. 1025-1034

Abstract

Several chiral polyfunctionalyzed cyclohexanones and cyclohexenones have been synthesized through Diels-Alder cycloadditions, stereoselectivity beingstated by X-ray structural analysis and NOE experiments. The chemoselectivity in the paladium(II)-catalyzed reaction between cyclohexenones and diazomethane has been investigated. Thus, in those enones bearing an amide function on the gamma -carbon, the preferential addition occurs at the carbonyl giving epoxides which, under acid conditions, rearrange to tetrahydrobenzoxazoles. The other cyclohexenones afford cyclopropanes as a result of addition to the C=C bond. A mechanistic approach to explain the whole process is proposed. (C) 2001 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 01/04/20 alle ore 11:50:15