2-Chloromethyl-3-(2-methoxyethoxy)propene: Naphthalene-catalysed lithiation and reaction towards electrophiles

Article abstract of DOI:10.1016/S0040-4039(98)00476-6

The reaction of the title compound (1) with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of an electrophile [E₁⁺=Bu(t)CHO, Et₂CO, (CH₂)₅CO, PhCOMe, Me₃SiCl] in THF at -78 to -30°C, followed by treatment with a second electrophile [E₂⁺=Bu(t)CHO, Me₂CO, Et₂CO, (CH₂)₄CO, (CH₂)₅CO, Bu(t)COMe, Bu(t)₂CO, PhCH=NPh, Me₃SiCl, D₂O] at -30°C to room temperature leads, after hydrolysis, to the expected compounds 2. For carbonyl derivatives, compounds 2 were successively hydroborated (BH₃·THF) and oxidised [33% H₂O₂ and then PCC or RuCl₂(PPh₃)₃] to give directly the corresponding perhydrofurofurans 4.