Atroposelective Chan-Evans-Lam Amination

ChemRxiv

Abstract

The synthetic control of atropoisomerism along C─N bonds is a major challenge, and methods that allow C─N atroposelective bond formation are rare. This is a problem because each atropoisomer can feature starkly differentiated biological properties. Yet, among the three most practical and applicable classical amination methods available: 1) the Cu-catalyzed Ullmann-Goldberg reaction, 2) the Pd-catalyzed Buchwald-Hartwig reaction, and 3) the Cu-catalyzed Chan-Evans-Lam reaction, none has truly been rendered atroposelective at the newly formed C─N bond. The first ever Chan-Evans-Lam atroposelective amination is herein described with a simple copper catalyst and new PyrOx chiral ligand. This method constitutes a change of paradigm in the field.

Authors 4

1. Vinzenz Thönnißen Aachen

   RWTH Aachen University

   Affiliation as printed

   RWTH Aachen University

2. Johannes Westphäling Aachen

   RWTH Aachen University

   Affiliation as printed

   RWTH Aachen University

3. Iuliana L. Atodiresei Aachen

   RWTH Aachen University

   Affiliation as printed

   RWTH Aachen University

4. Frédéric W. Patureau Aachen

   RWTH Aachen University

   Affiliation as printed

   RWTH Aachen University