Borohydride-polyethylene glycol monomethyl ether (borohydride-PEGMME) derivatives were prepared by allowing low molecular weight polyethylene glycol (M-w = 350) to react with either LiBH4, NaBH4, or KBH4. After comparing the reactivity of these borohydrides toward aldehydes, ketones, halides and esters, it was established that the LIBH4-PEGMME derivative was the most active and the least selective, the NaBH4-PEGMME derivative exhibited moderate reactivity and selectivity, and the KBH4-PEGMME derivative was the most selective and the least reactive. Additionally, the NaBH4-PEGMME derivative was further functionalized by the addition of a chiral alcohol or chiral amino alcohol to the borohydride ion. In all cases, the activity of the phase transfer moiety increased and the enantiomeric induction that resulted from the reduction of acetophenone was low to moderate (23-40% ee). An attempted elucidation of the active reagent indicated that a significant amount of unreacted sodium borohydride was present in the reaction mixture. The presence of this achiral reagent probably accounts for the more modest levels of chiral induction that were observed.