Functionalized organozincates and organocuprates derived from gamma-hydroxytellurides in the preparation of 1,4-hydroxyketones
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
|---|---|
| Data(s) |
20/10/2012
20/10/2012
2009
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| Resumo |
A C-O-dianionic zincate was generated by a Te/Li exchange reaction of an alkyltelluride, followed by Li/Zn transmetallation and reaction with methyllithium. The reaction between the enantiomerically pure (99% ee) (R)-dianionic zincate and benzoyl chloride led to 3-hydroxy-1-phenyl pentanone with total retention of the carbon configuration (99% ee). Similar results were obtained using the corresponding Lipshutz cyanocuprates. (C) 2009 Elsevier Ltd. All rights reserved. FAPESP Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) CNPq Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) CAPES |
| Identificador |
TETRAHEDRON LETTERS, v.50, n.46, p.6368-6371, 2009 0040-4039 http://producao.usp.br/handle/BDPI/31134 10.1016/j.tetlet.2009.08.097 |
| Idioma(s) |
eng |
| Publicador |
PERGAMON-ELSEVIER SCIENCE LTD |
| Relação |
Tetrahedron Letters |
| Direitos |
closedAccess Copyright PERGAMON-ELSEVIER SCIENCE LTD |
| Palavras-Chave | #Hydroxyltellurides #Organozincates #Organocuprates #1,4-Hydroxyketones #EXCHANGE-REACTIONS #LITHIUM EXCHANGE #TELLURIUM #ORGANOMETALLICS #IODINE #LICL #ARYLMAGNESIUM #COMPLEXES #CHEMISTRY #MECHANISM #Chemistry, Organic |
| Tipo |
article original article publishedVersion |
