125986-59-6

Upstream product

• 107-59-5 tert-Butyl chloroacetate 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 125950-99-4 tert-butyl (E)-3-(4-chlorophenyl)prop-2-enoate 

Relevant academic research and scientific papers

Synthesis of (E)-α,β-unsaturated esters and (Z)-vinyl halides with total or high diastereoselectivity by using samarium metal

A highly diastereoselective β-elimination of 2-halo-3-hydroxy esters 1 or O-acetylated 1,1-dihaloalkan-2-ols 4 is achieved with samarium in the presence of diiodomethane, yielding α,β-unsaturated esters 2 or vinyl halides 5, respectively. The β-elimination reaction was promoted by samarium diiodide, which was generated in situ. The starting halohydrins 1 or 4 are easily prepared by reaction of the corresponding lithium enolates of α-halo esters or dihalomethyllithium with aldehydes at -78°C. The influence of the reaction conditions and the structure of the starting compounds on the diastereoselectivity of the β-elimination reactions is discussed, A comparative study of the β-elimination reaction with preformed SmI2 and metallic samarium is also performed. These elimination reactions can be explained by the proposed mechanism. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

Synthesis of (E)-a,β-unsaturated esters and amides with total selectivity using samarium diiodide

β-elimination of α-halo-β-hydroxyesters 1 was achieved by using samarium diiodide as a metalating reagent, and afforded di- and trisubstituted (E)-α,βunsaturated esters 2 with total steroselectivity. This method has also been extended to the corresponding disubstituted (E)-α,β-unsaturated amides.

NEW SIMPLE METHOD OF SYNTHESIS OF SUBSTITUTED HALO ALKENES via KNOEVENAGEL-TYPE CONDENSATION OF ALDEHYDES WITH α-HALO-SUBSTITUTED CH-ACIDS

Condensation of t-butylchloroacetate or aryl halomethyl sulphone with aldehydes in the presence of base yields corresponding halohydrins that are easily converted into substituted halo alkenes with high E/Z selectivity.