Your browser doesn't support javascript.
loading
Total Stereoselective Michael Addition of N- and S- Nucleophiles to a d-Erythrosyl 1,5-Lactone Derivative. Experimental and Theoretical Studies Devoted to the Synthesis of 2,6-Dideoxy-4-functionalized-d- ribono-hexono-1,4-lactone.
Rocha, Juliana F; Freitas, David S; Noro, Jennifer; Silva Teixeira, Carla S; Sousa, Cristina E A; Alves, Maria J; Cerqueira, Nuno M F S A.
Afiliación
  • Rocha JF; REQUIMTE/UCIBIO, Departamento de Química e Bioquímica, Faculdade de Ciências , Universidade do Porto , Rua do Campo Alegre s/n , 4169-007 Porto , Portugal.
  • Freitas DS; Departamento de Química , Universidade do Minho , Campus de Gualtar , 4710-057 Braga , Portugal.
  • Noro J; Departamento de Química , Universidade do Minho , Campus de Gualtar , 4710-057 Braga , Portugal.
  • Silva Teixeira CS; REQUIMTE/UCIBIO, Departamento de Química e Bioquímica, Faculdade de Ciências , Universidade do Porto , Rua do Campo Alegre s/n , 4169-007 Porto , Portugal.
  • Sousa CEA; Departamento de Química , Universidade do Minho , Campus de Gualtar , 4710-057 Braga , Portugal.
  • Alves MJ; Departamento de Química , Universidade do Minho , Campus de Gualtar , 4710-057 Braga , Portugal.
  • Cerqueira NMFSA; REQUIMTE/UCIBIO, Departamento de Química e Bioquímica, Faculdade de Ciências , Universidade do Porto , Rua do Campo Alegre s/n , 4169-007 Porto , Portugal.
J Org Chem ; 83(15): 8011-8019, 2018 08 03.
Article en En | MEDLINE | ID: mdl-29924603
The synthesis of a 1,5-lactone 2,4- O-alkylidene-d-erythrose derivative was found to be a highly stereoselective template in Michael addition trough the reaction of a d-erythrosyl 1,5-lactone derivative with nitrogen and sulfur nucleophiles. The sulfur adducts formed are 1 (d-erythrose derivative):1 (nucleophile), and the nitrogen adducts are 1:2. Both were then treated under HCl to give 2,6-dideoxy-4-functionalized-d- ribono-hexono-1,4-lactone by a reaction cascade in high overall yield. Reaction's scale up even improves the yield. The theoretical and computational results clearly explain the origin of the stereoselectivity, and the energetic course of reactions starting with nitrogen and sulfide nucleophiles. Considering that the 1,4-lactones obtained in this work offer a new molecular scaffold for organic synthesis, these new results provide a solid theoretical platform that can be used to speed up synthesis of other derivatives in a stereo- and regioselective way.
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2018 Tipo del documento: Article País de afiliación: Portugal Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2018 Tipo del documento: Article País de afiliación: Portugal Pais de publicación: Estados Unidos