Abstract The regioselectivity of metallation of hexyl diisopropyl phosphate (1) depends on the solvent, the temperature, and the base used. The best results are obtained with s- BuLi/TMEDA in hexane and diethyl ether at-78° C. the CH2O group being deprotonated preferentially over the CHO group (3: 1 versus 2, 5: 1). The intermediate phosphonyloxy- substituted alkyllithiums (±)-4 and (±)-5 rearrange to phosphonates (±)-6 and (±)-7, ...
