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Titolo:
STEREOCONTROL IN DIELS-ALDER CYCLOADDITION TO UNSATURATED SUGARS - REACTIVITIES OF ACYCLIC 7-CARBON TRANS DIENOPHILES DERIVED FROM ALDOPENTOSES
Autore:
HORTON D; KOH D;
Indirizzi:
AMERICAN UNIV,DEPT CHEM,4400 MASSACHUSETTS AVE NW WASHINGTON DC 20016 OHIO STATE UNIV,DEPT CHEM COLUMBUS OH 43210
Titolo Testata:
Carbohydrate research
fascicolo: 2, volume: 250, anno: 1993,
pagine: 249 - 260
SICI:
0008-6215(1993)250:2<249:SIDCTU>2.0.ZU;2-U
Fonte:
ISI
Lingua:
ENG
Soggetto:
SUBSTITUTED CYCLOPENTANE DERIVATIVES; STEREOSELECTIVE SYNTHESIS; NORBORNENE DERIVATIVES; STEREOCHEMICAL CONTROL; ORGANIC-SYNTHESIS; CONFORMATIONS; DITHIOACETALS; SELECTIVITY; DIETHYL;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
28
Recensione:
Indirizzi per estratti:
Citazione:
D. Horton e D. Koh, "STEREOCONTROL IN DIELS-ALDER CYCLOADDITION TO UNSATURATED SUGARS - REACTIVITIES OF ACYCLIC 7-CARBON TRANS DIENOPHILES DERIVED FROM ALDOPENTOSES", Carbohydrate research, 250(2), 1993, pp. 249-260

Abstract

Acyclic trans-2,3-unsaturated aldoheptonate derivatives (1-9) obtained from D-aldopentoses by Wittig chain-extension served as dienophiles for a detailed comparative study of their asymmetric Diels-Alder cycloaddition with cyclopentadiene. Cycloaddition under uncatalyzed thermalconditions gave mixtures of the four possible stereoisomeric norbornene adducts. The endo:exo ratios and the diastereofacial selectivities in the formation of the adducts were determined by NMR spectroscopy and by chemical transformations. The quantitative distribution of adducts as a function of stereochemistry of the dienophile is discussed.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 01/12/20 alle ore 07:42:34