Photoredox-Catalyzed Synthesis of fl-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 beta-amino ethers and beta-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 alpha-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 alpha-alkoxy methyl radical and superoxide.