Add time:08/03/2019         Source:sciencedirect.com

The organozinc derivative (2a) of ethyl α-bromomethyl acrylate is not nucleophilic towards haloalkanes but can be alkylated with chlorotrimethylsilane. 2a is unreactive towards carbonoxygen single bonds and is unsuitable for conjugate addition (α-enones and α,β-ethylenic esters). Its acylation can be carried out in DME in the presence of palladium(0) catalyst. Reactions with carbonoxygen and carbonnitrogen double bonds permit the preparation of α-methylene γ-butyrolactones and lactams without the formation of side-products. This route is especially suitable for reactions with substrates such as imines that are both nucleophilic and electrophilic.

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