O-Benzoylhydroxylamines as Alkyl Nitrene Precursors: Synthesis of Saturated N-Heterocycles from Primary Amines

Org Lett. 2020 Nov 20;22(22):8769-8773. doi: 10.1021/acs.orglett.0c02842. Epub 2020 Sep 11.

Abstract

We introduce O-benzoylhydroxylamines as competent alkyl nitrene precursors. The combination of readily available, stable substrates and a proficient rhodium catalyst provides a straightforward means for the construction of various pyrrolidine rings from the corresponding primary amines. Preliminary mechanistic investigation suggests that the structure of the nitrene precursor plays a role in determining the nature of the resulting reactive intermediate.

Publication types

  • Research Support, Non-U.S. Gov't