Six- and five-membered 3-alkoxy-2-lithiocycloalkenes: new stable non-anionic β-functionalised organolithium compounds

Naphthalene-catalysed reductive lithiation of various functionalised chlorocycloalkenes leads to the corresponding non-anionic β-alkoxyfunctionalised organolithium reagents . Their reaction with different electrophiles, such as water, aldehydes, ketones and imines, gave the expected products and . The diastereoselection in the reaction with aldehydes can be modified by the use of different additives. In the case of using 3-methoxy-2-chlorocyclopentene () as starting material, and depending on reaction time, unexpected bicyclopentadiene derivatives were isolated, together with the expected compounds .