The reaction of 3-chloro-2-(chloromethyl)-1-propene (1) with lithium and a catalytic amount of naphthalene in the presence of different carbonyl compounds in THF a− 78dgC affords, after hydrolysis, the corresponding methylenic diols 2, which by a tandem hydroboration- oxidation with hydrogen peroxide followed by treatment with PCC (for ketone derivatives) or RuCl2 (PPh3) 3 (for aldehyde derivatives) yields the expected perhydrofurofurans 3.
