Photoredox-Catalyzed Synthesis of ß-Amino Alcohols: Hydroxymethylation of Imines with α-Silyl Ether as Hydroxymethyl Radical Precursor.

Carbon-carbon bond formation is an efficient approach for the synthesis of amino alcohols using two simple starting materials. Herein, we present a novel method for a divergent synthesis of ß-amino ethers and ß-amino alcohols in a sequential one-pot protocol under high-efficiency, mild, and metal- or metal-free conditions. Especially, TMSCH2OPMP was developed as a synthetic equivalent of α-hydroxymethyl radical in an in situ photocatalyzed oxidative PMP group deprotection strategy under air. A preliminary mechanistic investigation provides evidence for reaction mechanism involving a photoinduced α-alkoxy methyl radical and superoxide.