Chemoselective Synthesis of α-Tertiary Hydroxy Oximes via Photochemical 1,3-Boronate Rearrangement

Abstract

Tertiary alcohols with adjacent nucleophilic labile groups are prevalent in bioactive molecules but are challenging to synthesize. Herein we introduce a direct, protecting group-free method to access αtertiary hydroxy oximes via photochemical 1,3-boronate rearrangement. This reaction delivers high yields (up to 94%) using readily available boronic acids, is scalable to gram quantities, and allows for further derivatization to other nitrogen-containing molecules.