Communication

Overall “Pseudocationic” Trifluoromethylation of Dihydropyridines with Triflic Anhydride†

  1. Henri Rudler Dr.1,
  2. Andrée Parlier Dr.1,
  3. Cesar Sandoval-Chavez1,
  4. Patrick Herson Dr.1,
  5. Jean-Claude Daran Dr.2

Article first published online: 30 JUL 2008

DOI: 10.1002/anie.200801879

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 36, pages 6843–6846, August 25, 2008

Additional Information

How to Cite

Rudler, H., Parlier, A., Sandoval-Chavez, C., Herson, P. and Daran, J.-C. (2008), Overall “Pseudocationic” Trifluoromethylation of Dihydropyridines with Triflic Anhydride. Angew. Chem. Int. Ed., 47: 6843–6846. doi: 10.1002/anie.200801879

Author Information

  1. 1

    Laboratoire de Chimie Organique, UMR CNRS 7611, and Laboratoire de Chimie Inorganique et matériaux moléculaires UMR CNRS 7071, Université Pierre et Marie Curie, CC 47, 4 place jussieu, 75252 Paris cedex 5 (France), Fax: (+33) 1-4427-3787

  2. 2

    Laboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 4 (France)

  1. †

    We thank CONACYT Mexico for a grant to C.S.-C.

Publication History

  1. Issue published online: 20 AUG 2008
  2. Article first published online: 30 JUL 2008
  3. Manuscript Received: 22 APR 2008
  4. Manuscript Revised: 25 JUN 2006

Funded by

  • CONACYT Mexico

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Keywords:

  • heterocycles;
  • lactones;
  • synthetic methods;
  • trifluoromethylation
Thumbnail image of graphical abstract

A triflic reaction: The role of triflic anhydride is not limited to the transfer of a triflyl group to the nitrogen atom during the interaction of pyridine with bis(trimethylsilyl)ketene acetals: it can also provide an electrophilic CF3 group able to transform the formed dihydropyridines substituted with trimethylsilyl ester groups into α-trifluoromethyllactones (see scheme).

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