Aminoborohydrides. 14. Lithium aminoborohydrides in the selective reduction or amination of alkyl methanesulfonate esters

[GRAPHICS] Lithium amino borohydride (LAB) reagents initiate the amination or reductio n of alkyl methanesulfonate esters, as dictated by reaction conditions. Alk yl methanesulfonate esters treated with unhindered LABs provide tertiary am ines in excellent yield. Reduction to the corresponding alkane is achieved using a hindered LAB reagent or by forming the highly reactive Super-Hydrid e reagent in situ using LAB and a catalytic amount of triethylborane. The r eduction methodology disclosed herein is a safe and convenient alternative to existing synthetic methods.