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Atom Efficient Synthesis of Selectively Difluorinated Carbocycles through a Gold(I)-Catalyzed Cyclization.
McCarter, Adam W; Sommer, Magdalena; Percy, Jonathan M; Jamieson, Craig; Kennedy, Alan R; Hirst, David J.
Afiliação
  • McCarter AW; Department of Pure and Applied Chemistry , University of Strathclyde , 295 Cathedral Street , Glasgow G1 1XL , United Kingdom.
  • Sommer M; Department of Pure and Applied Chemistry , University of Strathclyde , 295 Cathedral Street , Glasgow G1 1XL , United Kingdom.
  • Percy JM; Department of Pure and Applied Chemistry , University of Strathclyde , 295 Cathedral Street , Glasgow G1 1XL , United Kingdom.
  • Jamieson C; Department of Pure and Applied Chemistry , University of Strathclyde , 295 Cathedral Street , Glasgow G1 1XL , United Kingdom.
  • Kennedy AR; Department of Pure and Applied Chemistry , University of Strathclyde , 295 Cathedral Street , Glasgow G1 1XL , United Kingdom.
  • Hirst DJ; GlaxoSmithKline R&D Ltd ., Gunnels Wood Road , Stevenage , Herts SG1 2NY , United Kingdom.
J Org Chem ; 83(16): 8888-8905, 2018 08 17.
Article em En | MEDLINE | ID: mdl-29978696
The intramolecular carbocyclization of difluorinated enol acetals has been achieved for the first time using gold(I) catalysis. Difluorinated enol acetals bearing a pendant alkene group can be cyclized and reduced in one pot to form fluorinated diol motifs. Alternatively, the cyclization of terminal alkynes allows for the synthesis of fluorinated pyran scaffolds. Both cyclization processes can be performed under mild conditions allowing access to complex products rich in functionality. The cyclic systems are synthesized concisely (maximum four steps) from trifluoroethanol, an inexpensive fluorinated feedstock.

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2018 Tipo de documento: Article País de afiliação: Reino Unido

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2018 Tipo de documento: Article País de afiliação: Reino Unido