3,5-Bis(trifluoromethyl)phenyl sulfones in the modified Julia olefination: application to the synthesis of resveratrol

Diego A. Alonso, Carmen Nájera* and Montserrat Varea

*Departamento de Química Orgánica, Universidad de Alicante, Apartado. 99, 03080, Alicante, Spain, H9R 4P8, Email: cnajeraua.es

D. A. Alonso, C. Nájera, M. Varea, Tetrahedron Lett., 2004, 45, 573-577.

DOI: 10.1016/j.tetlet.2003.10.196

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Abstract

The Julia-Kocienski olefination between alkyl 3,5-bis(trifluoromethyl)phenyl sulfon carbanions and aldehydes affords with good yields and stereoselectivities the corresponding 1,2-disubstituted alkenes. This one-pot protocol can be performed using KOH at room temperature or the phosphazene base P4-t-Bu at -78 °C, and has been successfully used in high yielding and stereoselective synthesis of various stilbenes.

see article for more examples

proposed mechanism

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Key Words

Julia Olefination, Sulfones, (Z/E)-Selectivity, Resveratrol

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ID: J72-Y2004-1000