Issue 46, 2020

Atroposelective synthesis of configurationally stable nonbiaryl N–C atropisomers through direct asymmetric aminations of 1,3-benzenediamines

Abstract

A highly atroposelective synthesis of nonbiaryl N–C atropisomers was achieved via direct aminations of 1,3-benzenediamines with azodicarboxylates enabled by chiral phosphoric acid catalysis. A series of N-substituents, benzene-substituents and azodicarboxylates were well tolerated, generating N–C atropisomers with high configurational stability. The facile derivatizations and utilizations of the chiral products as novel chiral organocatalysts demonstrate the value of these reactions.

Graphical abstract: Atroposelective synthesis of configurationally stable nonbiaryl N–C atropisomers through direct asymmetric aminations of 1,3-benzenediamines

Supplementary files

Article information

Article type
Communication
Submitted
02 Apr 2020
Accepted
24 Apr 2020
First published
24 Apr 2020

Chem. Commun., 2020,56, 6201-6204

Atroposelective synthesis of configurationally stable nonbiaryl N–C atropisomers through direct asymmetric aminations of 1,3-benzenediamines

D. Wang, Q. Jiang and X. Yang, Chem. Commun., 2020, 56, 6201 DOI: 10.1039/D0CC02368J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements