One-Pot, Three-Step Synthesis of Benzoxazinones via Use of the Bpin Group as a Masked Nucleophile

Org Lett. 2021 Apr 2;23(7):2720-2725. doi: 10.1021/acs.orglett.1c00623. Epub 2021 Mar 10.

Abstract

The utilization of the Bpin group as a pronucleophile to facilitate the assembly of cyclic carbamates has been achieved. This one-pot process involves an initial copper-catalyzed borylation, a subsequent C-B bond oxidation to generate the reactive alcohol intermediate, and a cyclization. We report the use of this efficient, scalable, and simple method toward the synthesis of a wide range of benzoxazinone scaffolds, including enantioselective results. Subsequent transformations into useful scaffolds showcase the utility of this strategy.