Trimethyl 2-phosphonoacrylate

CAS 55168-74-6, Cat. No EN300-221426
Michael acceptor and a phosphonate anion source

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Trimethyl 2-phosphonoacrylate is a highly versatile bifunctional vinyl phosphonate, acting as both a Michael acceptor and a phosphonate anion source¹. It readily undergoes conjugate addition with carbon, nitrogen, oxygen, and sulfur nucleophiles. Resulting phosphonate intermediates perform efficient HWE olefinations, enabling access to unsaturated esters, dienes, trienes, heterocycles, and carbocycles. It also serves as a useful enophile and dienophile under Lewis acid or thermal conditions. The reagent is widely applied in complex molecule synthesis, including carbapenems and natural products. It is easy to handle and soluble in common organic solvents.

Synonyms: methyl 2-(dimethoxyphosphinyl)acrylate; methyl 2-dimethoxyphosphorylprop-2-enoate; 2-(dimethoxy-phosphoryl)-acrylic acid methyl ester