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Triflic-Acid-Catalyzed Tandem Allylic Substitution-Cyclization Reaction of Alcohols with Thiophenols-Facile Access to Polysubstituted Thiochromans.
Vu, Minh Duy; Foo, Ce Qing; Sadeer, Abdul; Shand, Sam S; Li, Yongxin; Pullarkat, Sumod A.
Afiliación
  • Vu MD; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
  • Foo CQ; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
  • Sadeer A; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
  • Shand SS; School of Chemistry, University of Edinburgh, Joseph Black Building, West Mains Road, Edinburgh EH9 3JJ, Scotland.
  • Li Y; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
  • Pullarkat SA; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
ACS Omega ; 3(8): 8945-8951, 2018 Aug 31.
Article en En | MEDLINE | ID: mdl-31459027
Hitherto inaccessible multisubstituted thiochroman derivatives were constructed via the one-pot reaction of thiophenols with allylic alcohols catalyzed by 0.2 equiv triflic acid under metal-free conditions. A variety of thiochroman derivatives can be obtained by this straightforward protocol that allows the introduction of up to four substituents at various locations on the thiochroman skeleton. Relative conformations of all isolated products were confirmed by NOESY NMR studies, and a stepwise mechanism, proceeding via an allylic substitution-intramolecular cyclization protocol, is proposed on the basis of NMR experiments.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: ACS Omega Año: 2018 Tipo del documento: Article País de afiliación: Singapur Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: ACS Omega Año: 2018 Tipo del documento: Article País de afiliación: Singapur Pais de publicación: Estados Unidos