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Titolo:
ENANTIOMER DIFFERENTIATION IN INTRAMOLECULAR CARBON-HYDROGEN INSERTION REACTIONS OF RACEMIC SECONDARY ALKYL DIAZOACETATES CATALYZED BY CHIRAL DIRHODIUM(II) CARBOXAMIDATES
Autore:
DOYLE MP; KALININ AV;
Indirizzi:
TRINITY UNIV,DEPT CHEM SAN ANTONIO TX 78212 RUSSIAN ACAD SCI,ND ZELINSKII ORGAN CHEM INST MOSCOW 117913 RUSSIA
Titolo Testata:
Russian chemical bulletin
fascicolo: 9, volume: 44, anno: 1995,
pagine: 1729 - 1734
SICI:
1066-5285(1995)44:9<1729:EDIICI>2.0.ZU;2-W
Fonte:
ISI
Lingua:
ENG
Soggetto:
GAMMA-LACTONES; CARBOXYLATES;
Keywords:
KINETIC RESOLUTION; CHIRAL DIRHODIUM(II) CARBOXAMIDATES; ENANTIOSELECTIVE CARBON-HYDROGEN INSERTION; GAMMA-LACTONE FORMATION; DIASTEREOSELECTIVE CARBON-HYDROGEN INSERTION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
15
Recensione:
Indirizzi per estratti:
Citazione:
M.P. Doyle e A.V. Kalinin, "ENANTIOMER DIFFERENTIATION IN INTRAMOLECULAR CARBON-HYDROGEN INSERTION REACTIONS OF RACEMIC SECONDARY ALKYL DIAZOACETATES CATALYZED BY CHIRAL DIRHODIUM(II) CARBOXAMIDATES", Russian chemical bulletin, 44(9), 1995, pp. 1729-1734

Abstract

Highly efficient kinetic resolution of racemic secondary alkyl diazoacetates in intramolecular carbon-hydrogen insertion reactions has beenachieved using chiral dirhodium(II) carboxamidates. Products formed from catalytic diazo decomposition of racemic 2-octyl diazoacetate and,separately, its (2R)- and (2S)-enantiomeric forms, as well as both cis- and trans-2-methylcyclohexyl diazoacetates, have been systematically evaluated. Enantioselectivities up to 99 % ee have been obtained forgamma-lactone formation. beta-lactone production has been observed and, although minor with cyclohexyl diazoacetates, is the major insertion pathway for diazo decomposition of 2-octyl diazoacetate.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 07/04/20 alle ore 23:06:43