γ-Functionalised β-methylene organolithium compounds from 3-chloro-2-(chloromethyl)propene: Synthetic applications

Article abstract of DOI:10.1016/S0040-4020(01)80206-4

The reaction of functionalised methallylic chlorides 1 with an excess of lithium powder and a catalytic amount of naphthalene (8 mol%) in the presence of a carbonyl compound (Barbier-type conditions) at -78°C leads, after hydrolysis with water, to the corresponding polyfunctionalised compounds 2. Starting materials 1 are easily available from 3-chloro-2-(chloromethyl)propene by nucleophilic substitution.