Tetrahedron Letters p. 2187 - 2190 (1997)
Update date:2022-07-30
Topics:
Alonso, Francisco
Lorenzo, Emilio
Yus, Miguel
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 -78°C 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.
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