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Improved Julia−Kocienski Conditions for the Methylenation of Aldehydes and Ketones

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Christophe Aïssa

Max-Planck-Institut fr Kohlenforschung, D-45470 Mlheim/Ruhr, Germany aissa@mpi-muelheim.mpg.de

J. Org. Chem., 2006, 71 (1), pp 360–363

DOI: 10.1021/jo051693a

Publication Date (Web): November 23, 2005

Abstract

The scope of the methylenation of aldehydes and ketones under optimized Julia−Kocienski conditions is broadened by using 1-tert-butyl-1H-tetrazol-5-ylmethyl sulfone. Two different Barbier-type procedures are applied with NaHMDS at −78 °C or Cs₂CO₃ at 70 °C. The latter conditions are also adapted for the preparation of 1,2-disubstituted olefins and intramolecular olefination reactions.

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Published In Issue January 06, 2006
Received August 10, 2005

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Improved Julia−Kocienski Conditions for the Methylenation of Aldehydes and Ketones

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Enantiospecific Total Syntheses of Kapakahines B and F

Total Synthesis of (−)-Acutumine

3,5-Bis(trifluoromethyl)phenyl Sulfones in the Direct Julia−Kocienski Olefination

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