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

Christophe Aïssa*

*Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany, aissampi-muelheim.mpg.de

C. Aïssa, J. Org. Chem., 2006, 71, 360-363.

DOI: 10.1021/jo051693a

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Abstract

The methylenation of aldehydes and ketones under optimized Julia-Kocienski conditions was conducted by using 1-tert-butyl-1H-tetrazol-5-ylmethyl sulfone with either 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 olefinations.

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Key Words

Terminal Olefins, Julia-Kocienski Olefination

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ID: J42-Y2006-100