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Issue 28, 2019
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Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles

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Abstract

Central-to-axial chirality conversion provides efficient access to axially chiral compounds, and several examples regarding the conversion of one, two or four stereocenters to one axis have been reported. Herein, we report the conversion of two stereocenters to one or two chiral axes for the first time. In this study, a new class of enantiomerically enriched 2,3-diarylbenzoindoles was efficiently synthesized using a chiral phosphoric acid-catalyzed [3 + 2] formal cycloaddition and a mild DDQ oxidation strategy. Moreover, a speculative model of the central-to-axial chirality conversion outcome was proposed based on preliminary mechanistic studies and DFT calculations. Potentially, using this strategy, useful chiral phosphine ligand can be synthesized smoothly (99% ee).

Graphical abstract: Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles

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Supplementary files

Article information


Submitted
16 Feb 2019
Accepted
09 May 2019
First published
20 May 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 6777-6784
Article type
Edge Article

Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles

Y. Hu, Z. Wang, H. Yang, J. Chen, Z. Wu, Y. Lei and L. Zhou, Chem. Sci., 2019, 10, 6777
DOI: 10.1039/C9SC00810A

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