Site-Specific Functionalization of 1,3-Dioxolane with Imines: A Radical Chain Approach to Masked α-Amino Aldehydes.

Abstract

A thiol-promoted site-specific addition of 1,3-dioxolane to imines through a radical chain process is described. This process represents a metal-free and redox-neutral way to convert inexpensive materials to a broad range of protected α-amino aldehydes in good to excellent yields using only a catalytic amount of radical precursor. Control experiments revealed that both the thiol and a small amount of oxygen from air are indispensable to the success of this reaction.