Issue 44, 2021

Organocatalytic cycloaddition–elimination cascade for atroposelective construction of heterobiaryls

Abstract

The first chiral phosphoric acid (CPA) catalyzed cycloaddition–elimination cascade reaction of 2-naphthol- and phenol-derived enecarbamates with azonaphthalenes has been established, providing a highly atroposelective route to an array of axially chiral aryl-C3-benzoindoles in excellent yields with excellent enantioselectivities. The success of this strategy derives from the stepwise process involving CPA-catalyzed asymmetric formal [3 + 2] cycloaddition and subsequent central-to-axial chirality conversion by elimination of a carbamate. In addition, the practicality of this reaction had been verified by varieties of transformations towards functionalized atropisomers.

Graphical abstract: Organocatalytic cycloaddition–elimination cascade for atroposelective construction of heterobiaryls

Supplementary files

Article information

Article type
Edge Article
Submitted
17 Sep 2021
Accepted
28 Oct 2021
First published
30 Oct 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 14920-14926

Organocatalytic cycloaddition–elimination cascade for atroposelective construction of heterobiaryls

W. Xu, W. Zhao, R. Zhang, J. Chen and L. Zhou, Chem. Sci., 2021, 12, 14920 DOI: 10.1039/D1SC05161J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements