Copper- and Chiral Nitroxide-Catalyzed Oxidative Kinetic Resolution of Axially Chiral N-Arylpyrroles

Lenin Kumar Verdhi, Natalia Fridman, Alex M. Szpilman

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

A readily prepared C2-symmetric, α-hydrogen-substituted chiral hydroxylamine serves as a precatalyst to generate a chiral nitroxide in situ. This chiral nitroxide catalyst in combination with a copper co-catalyst functions as an oxidant for an unprecedented enantioselective oxidative kinetic resolution (OKR) of racemic axially chiral N-arylpyrrole alcohols using atmospheric oxygen as an environmentally friendly terminal oxidant. The OKR process provides the axially chiral N-arylpyrroles in er up to 3.5:96.5 and with s factors up to 24.

Original languageEnglish
Pages (from-to)5078-5083
Number of pages6
JournalOrganic Letters
Volume24
Issue number28
DOIs
StatePublished - 22 Jul 2022

Fingerprint

Dive into the research topics of 'Copper- and Chiral Nitroxide-Catalyzed Oxidative Kinetic Resolution of Axially Chiral N-Arylpyrroles'. Together they form a unique fingerprint.

Cite this