3-chloropropyl phenyl ether as a 1,3-dilithiopropane source: Sequential reaction with carbonyl compounds

The reaction of 3-chloropropyl phenyl ether (1) with lithium powder and a catalytic amount of DTBB (2.5% molar) in THF at -78 degrees C followed by successive treatment with a carbonyl compound [E-1 = (BuCHO)-C-t, Me2CO, (CH2)(5)CO] at -78 to 20 degrees C and, after 1 h at this temperature, a second one [E-2 = (BuCHO)-C-t, PhCHO, MeCOPrn, (CH2)(5)CO] at -78 degrees C leads, after hydrolysis with water, to the formation of the corresponding 1,5-diols (2), in which two different electrophilic fragments have been introduced. (C) 1999 Elsevier Science Ltd. All rights reserved.