Journal of Organometallic Chemistry p. 157 - 168 (1988)
Update date:2022-07-29
Topics:
Alami, N. El.
Belaud, C.
Villieras, J.
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 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 nucle ophilic and electrophilic.
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