Categories: C=C Bond Formation >
Synthesis of (E)-alkenes
Name Reactions
Schlosser Modification of the Wittig Reaction
Recent Literature
The efficient olefination from organozinc reagents with aldehydes is
exploited in a new synthesis of aryl and alkyl olefins.
J.-X. Wang, Y. Fu, Y. Hu, K. Wang, Synthesis, 2003, 1506-1510.
Aryl tosylhydrazones react with t-BuOK, ClFeTPP, (MeO)3P,
and aldehydes to furnish olefins with high E selectivity through a
Wittig-type pathway via the corresponding diazo compounds, metal carbenes
and phosphorous ylides. A Horner-Wadsworth-Emmons-type reaction of ethyl
diazoacetate with aldehydes occurs with high E selectivity in the
presence of LiBr via the phosphonate anion, formed through an Arbuzov
reaction under completely base-free conditions.
V. K. Aggarwal, J. R. Fulton, C. G. Sheldon, J. de Vicente, J. Am. Chem. Soc., 2003, 125, 6034-6035.
A modification of the classical Julia-Lythgoe olefination using
sulfoxides instead of sulfones affords 1,2-di-, tri-, and tetrasubstituted
olefins in moderate to excellent yields and E/Z selectivity. The mild
conditions involve in situ benzoylation and SmI2/HMPA-mediated reductive elimination
as key steps.
J. Pospisil, T. Pospisil, I. E. Marko, Org. Lett., 2005, 7, 2373-2376.
A versatile and operationally simple base-catalyzed multi-component domino
reaction between α,β-unsaturated carbonyl compounds, aldehydes, and alcohols is
described, providing a new efficient, and stereoselective one-pot preparation of
trisubstituted alkenes and 1,3-dienes.
H. Habib-Zahmani, S. Hacini, C. Bories, J. Rodriguez, Synthesis, 2005,
2151-2156.
Fe(0) is cost-effective, environmentally friendly alternative to Cr(II) for
the olefination of carbonyls by activated polyhalides. Fe(0) proved
compatible with a wide range of functionality, such as unprotected phenol,
aryl nitro, carboxylic acid, and alkyl nitrile.
J. R. Falck, R. Bejot, D. K. Barma, A. Bandyopadhyay, S. Joseph, C.
Mioskowski, J. Org. Chem., 2006, 71, 8178-8182.
A domino oxidation of primary alcohols gives α,β-unsaturated compounds using the
combination of PCC-NaOAc and stabilized Wittig reagents.
J. Shet, V. Desai, S. Tilve, Synthesis,
2004,
1859-1863.
A series of vinyl sulfonamides was synthesized using the Horner reaction of
aldehydes and diphenylphosphorylmethanesulfonamide. The sulfonamide reagent was
easily prepared and can be stored indefinitely.
D. C. Reuter, J. E. McIntosh, A. C. Guinn, A. M. Madera, Synthesis, 2003, 2321-2324.
