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A Stereoselective Synthesis of trans-1,2-Disubstituted Alkenes Based on the Condensation of Aldehydes with Metallated 1-Phenyl-1H-tetrazol-5-yl Sulfones

Paul R. Blakemore, William J. Cole, Philip J. Kocieński*, Andrew Morley

*School of Chemistry, University of Leeds, Leeds LS2 9JT, U.K., Email:

P. R. Blakemore, W. J. Cole, P. J. Kocienski, A. Morley, Synlett, 1998, 26-28.

DOI: 10.1055/s-1998-1570


The reaction of metallated 1-phenyl-1H-tetrazol-5-yl sulfones and aldehydes gives good yields and stereoselectivity of trans-1,2-disubstituted alkenes when potassium or sodium hexamethyldisilazide is used as base and 1,2-dimethoxyethane is used as solvent.

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Key Words

alkene synthesis, heterocyclic sulfones, aldehydes, Julia-Kocienski olefination, tetrazole, benzothiazole

ID: J60-Y1998-320