Studies on chemo- and diastereo-selectivity of the Diels-Alder reactions of sulfinyltoluquinones with cyclopentadiene
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
|---|---|
| Data(s) |
20/10/2012
20/10/2012
2009
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| Resumo |
Sulfinyltoluquinones (2a-2c) were submitted to thermal or catalyzed [4+2] cycloaddition reactions with cyclopentadiene. For p-tolylsulfinyltoluquinones (2b) and (2c), almost complete C2-C3-chemo- and unlike-diastereoselectivity was achieved by catalysis with ZnBr(2), yielding adducts 6. Under thermal conditions, Diels-Alder reaction took place at the C5-C6 double bonds of quinones 2a-2c, generating mixtures of diastereoisomeric like- and unlike-adducts 4. Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES) |
| Identificador |
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, v.87, n.8, p.1135-1143, 2009 0008-4042 http://producao.usp.br/handle/BDPI/31507 10.1139/V09-070 |
| Idioma(s) |
eng |
| Publicador |
NATL RESEARCH COUNCIL CANADA-N R C RESEARCH PRESS |
| Relação |
Canadian Journal of Chemistry-revue Canadienne de Chimie |
| Direitos |
restrictedAccess Copyright NATL RESEARCH COUNCIL CANADA-N R C RESEARCH PRESS |
| Palavras-Chave | #Diels-Alder reaction #sulfinyltoluquinones #sulfinyl group #stereochemical control #pi-facial selectivity #TRIQUINANE NATURAL-PRODUCTS #ABSOLUTE-CONFIGURATION #COLOMBIASIN-A #ASYMMETRIC-SYNTHESIS #RUBIGINONES A(2) #ANTIBIOTICS #SULFOXIDES #SULFINYL #SYSTEM #ACID #Chemistry, Multidisciplinary |
| Tipo |
article original article publishedVersion |
