Synthesis of alkenes by anti-eliminations

Name Reactions

Recent Literature

Heating with NaI and DBU in dimethoxyethane effected clean elimination of tosylates to terminal olefins. This simple one-pot procedure was also applied to tosylates derived from an Evans Aldol Reaction.
P. Phukan, M. Bauer, M. E. Maier, Synthesis, 2003, 1324-1328.

The preparation of any length alkenyl halide from inexpensive starting reagents is reported. Standard organic transformations were used to prepare straight chain α-olefin halides in excellent overall yields with no detectable olefin isomerization and full recovery of any unreacted starting material.
T. W. Baughman, J. C. Sworen, K. B. Wagener, Tetrahedron, 2004, 60, 10943-10948.

The use of SmI₂ in the reductive elimination of 1,2-acetoxy sulfones (Julia-Lythgoe olefination) and the reductive cleavage of vinyl sulfones is reported.
G. E. Keck, K. A. Savin, M. Weglarz, J. Org. Chem., 1995, 60, 3194-3204.

Samarium diiodide promotes a photoinduced metalation of nonactivated C-Cl bonds of O-acetyl chlorohydrins and a β-elimination which affords alkenes with total or high stereoselectivity.
J. M. Concellón, H. Rodriguez-Solla, C. Simal, M. Huerta, Org. Lett., 2005, 7, 5833-5835.

A samarium-promoted synthesis of (E)-nitroalkenes from 1-bromo-1-nitroalkan-2-ols in high yields together with an efficient preparation of the 1-bromo-1-nitroalkan-2-ols constitutes a simple and advantageous alternative toward nitroalkenes with total E-stereoselectivity. A mechanism is proposed to explain the E-stereoselectivity of the β-elimination reaction.
J. M. Concellón, P. L. Bernad, H. Rodríguez-Solla, C. Concellón, J. Org. Chem., 2007, 72, 5451-5423.

A zinc carbenoid-mediated chain extension of β-dicarbonyl compounds provides access to α,β-unsaturated-γ-keto esters and amides with complete E selectivity via an intermediate zinc enolate, which is treated sequentially with iodine and DBU.
M. D. Ronsheim, C. K Zercher, J. Org. Chem., 2003, 68, 4535-4538.