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Optically active calixarenes conduced by methylene substitution.
Gopalsamuthiram, Vijay; Predeus, Alexander V; Huang, Rui H; Wulff, William D.
Afiliação
  • Gopalsamuthiram V; Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
J Am Chem Soc ; 131(50): 18018-9, 2009 Dec 23.
Article em En | MEDLINE | ID: mdl-19928964
The first method for the synthesis of optically active calix[4]arenes that are chiral as a result of substitution on the methylene bridges is described. The key step in the synthesis involves the reaction of a biscarbene complex with a diyne, which generates two of the benzene rings and the macrocyclic ring of the calix in a single transformation. The utility of this triple annulation process is demonstrated in the synthesis of di- and tetramethoxycalix[4]arenes. The flexibility of this synthetic approach is demonstrated by the synthesis of two diastereomers of the tetramethoxycalix[4]arenes in which each is synthesized in a stereoselective fashion by proper control of the absolute configurations of the methoxy groups in the biscarbene complex and in the diyne.

Texto completo: 1 Base de dados: MEDLINE Idioma: En Revista: J Am Chem Soc Ano de publicação: 2009 Tipo de documento: Article País de afiliação: Estados Unidos

Texto completo: 1 Base de dados: MEDLINE Idioma: En Revista: J Am Chem Soc Ano de publicação: 2009 Tipo de documento: Article País de afiliação: Estados Unidos