Selectride-Mediated Cleavage of 3-Picolyl and 3-Picolyloxycarbonyl Groups.

We report the selective cleavage of 3-pyridylmethyl (3-Pic) groups mediated by Selectride. The cleavage proceeds under mild conditions with short reaction times and is operationally simple. We have demonstrated the utility of this transformation for the protection of common functional groups as 3-Pic derivatives; for amines, we also applied protection as the 3-picolyloxycarbonyl group. Readily available reagents, combined with their unique selectivity, render this transformation a versatile addition to the organic chemist's protecting group toolbox.