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Titolo:
TRICARBONYLS - REACTIVE MODEL DIENOPHILES FOR ASYMMETRIC DIELS-ALDER REACTIONS
Autore:
LEHMLER HJ; NIEGER M; BREITMAIER E;
Indirizzi:
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1 D-53121 BONNGERMANY UNIV BONN,INST ANORGAN CHEM D-53121 BONN GERMANY
Titolo Testata:
Synthesis
fascicolo: 1, , anno: 1996,
pagine: 105 -
SICI:
0039-7881(1996):1<105:T-RMDF>2.0.ZU;2-1
Fonte:
ISI
Lingua:
ENG
Soggetto:
ENANTIOSELECTIVE SYNTHESIS; 4-NITROCYCLOHEXANONES; CYCLOADDITION; DERIVATIVES; ETHERS;
Keywords:
HETERO-DIELS-ALDER REACTION; 2-METHYL-1-(1-PHENYLALKOXY)1,3-BUTADIENES; INDANETRIONE; ALLOXANE; DIMETHYLDIOXIRANE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
52
Recensione:
Indirizzi per estratti:
Citazione:
H.J. Lehmler et al., "TRICARBONYLS - REACTIVE MODEL DIENOPHILES FOR ASYMMETRIC DIELS-ALDER REACTIONS", Synthesis, (1), 1996, pp. 105

Abstract

The hetero-Diels-Alder reaction of 2-methyl-1-(1-phenylalkoxy)-butadienes 5a-d with cyclic triketones proceeds smoothly at room temperaturein excellent yield and high diastereoselectivity. The configuration of the cycloadducts 6a and 6b was determined by X-ray single crystal analysis. Mild acidic hydrolysis of the cycloadduct 6a using SiO2 as a promoter yielded an alpha,beta-unsaturated aldehyde trans-9. The trans-epoxides 10 a-d can be obtained from 6a-d using a freshly prepared solution of dimethyldioxirane in acetone.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 30/11/20 alle ore 16:05:47