Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls

Hui Yang, Huai-Ri Sun, Rui-Qing He, Le Yu, Wei Hu, Jie Chen, Sen Yang, Gong-Gu Zhang and Ling Zhou ()
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Hui Yang: National Demonstration Center for Experimental Chemistry Education, Northwest University
Huai-Ri Sun: National Demonstration Center for Experimental Chemistry Education, Northwest University
Rui-Qing He: National Demonstration Center for Experimental Chemistry Education, Northwest University
Le Yu: National Demonstration Center for Experimental Chemistry Education, Northwest University
Wei Hu: National Demonstration Center for Experimental Chemistry Education, Northwest University
Jie Chen: National Demonstration Center for Experimental Chemistry Education, Northwest University
Sen Yang: National Demonstration Center for Experimental Chemistry Education, Northwest University
Gong-Gu Zhang: National Demonstration Center for Experimental Chemistry Education, Northwest University
Ling Zhou: National Demonstration Center for Experimental Chemistry Education, Northwest University

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract The axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands. Atroposelective indole formation is an efficient method to construct indole-based biaryls. We report herein the result of a chiral phosphoric acid catalyzed asymmetric cycloaddition of 3-alkynylindoles with azonaphthalenes. A class of indole-based biaryls were prepared efficiently with excellent yields and enantioselectivities (up to 98% yield, 99% ee). Control experiment and DFT calculations illustrate a possible mechanism in which the reaction proceeds via a dearomatization of indole to generate an allene-iminium intermediate, followed by an intramolecular aza-Michael addition. This approach provides a convergent synthetic strategy for enantioselective construction of axially chiral heterobiaryl backbones.

Date: 2022
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DOI: 10.1038/s41467-022-28211-0

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