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

Abstract

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 β-amino ethers and β-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 <i>in situ</i> 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.