Synthesis of (Z)-alkenes

Name Reactions

Recent Literature

N-sulfonyl imines undergo olefination reactions with various benzylidenetriphenylphosphoranes or allylidenetriphenylphosphoranes under mild reaction conditions to afford an array of both Z- and E-isomers of conjugated alkenes in good to excellent yields and with greater than 99:1 stereoselectivity depending on the N-sulfonyl group.
D.-J. Dong, H.-H. Li, S.-K. Tian, J. Am. Chem. Soc., 2010, 132, 5018-5020.

D.-J. Dong, H.-H. Li, S.-K. Tian, J. Am. Chem. Soc., 2010, 132, 5018-5020.

Deprotonation of 3,3,3-trichloropropyl-1-triphenylphosphonium chloride generates the corresponding phosphorane, which reacts with aldehydes to give trichloromethylated (Z)-olefins, which are useful for the synthesis of (Z)-1,3-enynes, (Z,Z)-1-chloro-1,3-dienes, and 1,3-diynes in high yields and stereospecificities.
M. S. Karatholuvhu, P. L. Fuchs, J. Am. Chem. Soc., 2004, 126, 14314-14315.

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.