Methyl (Z)-3-bromo-3-(4-methylbenzenesulfonyl)prop-2-enoate: Synthesis and reactions with dimethyl malonate and methyl acetoacetate

作者：Vasin V A; Bolusheva I Yu; Razin V V; Kapkaeva S R; Petrov P S; Somov N V

来源：Russian Journal of Organic Chemistry, 2016, 52(3): 299-306.

DOI：10.1134/S1070428016030015

Bromination-dehydrobromination of methyl (E)-3-(4-methylbenzenesulfonyl)prop-2-enoate gave methyl (Z)-3-bromo-3-(4-methylbenzenesulfonyl)prop-2-enoate whose structure was determined by X-ray analysis. Methyl (Z)-3-bromo-3-(4-methylbenzenesulfonyl)prop-2-enoate behaved as a synthetic equivalent of methyl 3-(4-methylbenzenesulfonyl)prop-2-ynoate in reactions with dimethyl malonate and methyl acetoacetate, which afforded the corresponding Michael adducts, trimethyl 3-(4-methylbenzenesulfonyl)prop-1-ene-1,1,2-tricarboxylate and dimethyl (Z)-2-acetyl-3-(4-methylbenzenesulfonyl)but-2-enedioate, respectively, via nucleophilic attack on the beta-position with respect to the sulfonyl group.

• 出版日期2016-3