191018-96-9

Upstream product

• 367-27-1 2,4-difluorophenol 
• 31460-11-4 (methoxycarbonylmethyl)phosphonic dichloride 
• 96-32-2 bromoacetic acid methyl ester 
• 191018-98-1 methyl bis(2,4-difluorophenyl) phosphite 
• 67605-34-9 methyl 2-(bis((trimethylsilyl)oxy)phosphoryl)acetate 

Downstream Products

• 38447-05-1 methyl (2Z,4E)-5-phenylpenta-2,4-dienoate 
• 689-89-4 (2E,4E)-methylhexa-2,4-dienoate 
• 6932-46-3 (2Z,4E)-hexadienoic acid methyl ester 
• 75128-90-4 (2Z)-decenoic acid methyl ester 
• 7367-85-3 methyl (E)-dec-2-enoate 
• 19310-31-7 methyl (Z)-3-(4-nitrophenyl)-2-propenoate 
• 19713-73-6 methyl (2Z)-3-phenylprop-2-enoate 
• 103-26-4 Methyl cinnamate 
• 7367-81-9 methyl (E)-oct-2-enoate 
• 68854-59-1 2-cis octenoic acid methyl ester 
• 19310-29-3 3-(4-methoxyphenyl)acrylic acid methyl ester 

Relevant academic research and scientific papers

Highly cis-selective Horner-Wadsworth-Emmons (HWE) reaction of methyl bis(2,4-difluorophenyl) phosphonoacetate

Of the previously reported Homer-Wadsworth-Emmons (HWE) reaction, the olefination of methyl bis(2,4-difluorophenyl)phosphonoacetate (1a) with various aldehydes gave unsaturated esters in the highest cis-selectivity.

Facile Two-Step Synthesis of Methyl Bis(2,2,2-trifluoroethyl)phosphonoacetate by Exploiting Garegg-Samuelsson Reaction Conditions

A facile two-step synthesis of methyl bis(2,2,2-trifluoroethyl)phosphonoacetate (Still-Gennari reagent) has been developed by exploiting Garegg-Samuelsson reaction conditions. Starting from trimethyl phosphonoacetate, Still-Gennari reagent was prepared in 94% yield via methyl 2-{bis[(trimethylsilyl)oxy]phosphoryl}acetate intermediate. This synthetic procedure was also used to prepare some kinds of Horner-Wadsworth-Emmons reagents and related compounds.

A study on the Z-selective Horner-Wadsworth-Emmons (HWE) reaction of methyl diarylphosphonoacetates

Experimental and theoretical studies were conducted to explore the Z-selectivities in the Horner-Wadsworth-Emmons (HWE) reaction employing several methyl diarylphosphonoacetates (3, 4, 5 and 6) and aldehydes. The Z-selectivity depended upon the reaction conditions such as the bases, reaction temperature, and the aromatic substituents on the phosphorus atoms but the almost phosphonoacetates used in the present study showed Z-selectivity in the reactions with both aromatic and aliphatic aldehydes. While the phosphonoacetate (3) with bis(2,4-difluorophenyl)phosphono group showed the highest Z-selectivity in all reaction conditions employed, decrease of the selectivity was observed in the case of some phosphonoacetates with diarylphosphono groups. These experimental results and the theoretical studies calculated by AM1 or 3-21G* ab initio methods suggested that the steric effect in the transition states of the addition steps was important rather than the electronic effect. A different aspect of the reaction courses between the Wittig and HWE reactions in the present computational chemistry was also described.