2-CHLOROMETHYL-3-(2-METHOXYETHOXY)PROPENE - NAPHTHALENE-CATALYZED LITHIATION AND REACTION TOWARDS ELECTROPHILES

The reaction of the title compound (1) with an excess of lithium powde r and a catalytic amount of naphthalene (2.5%) in the presence of an e lectrophile [E-1(+)=(BuCHO)-C-t, Et2CO, (CH2)(5)CO, PhCOMe, Me3SiCl] i n THF at -78 to -30 degrees C, followed by treatment with a second ele ctrophile [E-2(+)=(BuCHO)-C-t, Me2CO, Et2CO, (CH2)(4)CO, (CH2)(5)CO, ( BuCOMe)-C-t, (Bu2CO)-C-t, PhCH=NPh, Me3SiCl, D2O] at -30 degrees 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. (C) 1998 Elsevie r Science Ltd. All rights reserved.