Palladium-catalyzed asymmetric [3 + 2] cycloaddition of vinyl aziridines and α,β-unsaturated imines generated in situ from aryl sulfonyl indoles

Shan Xiao; Bo Chen; Qin Jiang; Long He; Wen-Dao Chu; Cheng-Yu He; Quan-Zhong Liu

doi:10.1039/D1QO00408E

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Palladium-catalyzed asymmetric [3 + 2] cycloaddition of vinyl aziridines and α,β-unsaturated imines generated in situ from aryl sulfonyl indoles†

Shan Xiao,^a Bo Chen,^a Qin Jiang,^a Long He,^b Wen-Dao Chu,

*^a Cheng-Yu He

*^a and Quan-Zhong Liu*^a

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* Corresponding authors

^a Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, China
E-mail: chuwendaonpo@126.com, hecy@cwnu.edu.cn, quanzhongliu@cwnu.edu.cn

^b College of Chemistry and Materials Engineering, Guiyang University, Guiyang 550005, China

Abstract

Palladium-catalyzed asymmetric formal [3 + 2] cycloaddition of vinyl aziridines and in situ generated unsaturated imines proceeded smoothly in the presence of chiral diphosphine ligands. The corresponding highly functionalized and optically enriched aza-spiroindolenines are obtained in up to 83% yield and with up to 97% ee and 13 : 1 dr.

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Article information

DOI: https://doi.org/10.1039/D1QO00408E
Article type: Research Article
Submitted: 13 Mar 2021
Accepted: 23 Apr 2021
First published: 26 Apr 2021

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Org. Chem. Front., 2021,8, 3729-3733

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Palladium-catalyzed asymmetric [3 + 2] cycloaddition of vinyl aziridines and α,β-unsaturated imines generated in situ from aryl sulfonyl indoles

S. Xiao, B. Chen, Q. Jiang, L. He, W. Chu, C. He and Q. Liu, Org. Chem. Front., 2021, 8, 3729 DOI: 10.1039/D1QO00408E

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Organic Chemistry Frontiers

Palladium-catalyzed asymmetric [3 + 2] cycloaddition of vinyl aziridines and α,β-unsaturated imines generated in situ from aryl sulfonyl indoles†

Abstract

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Palladium-catalyzed asymmetric [3 + 2] cycloaddition of vinyl aziridines and α,β-unsaturated imines generated in situ from aryl sulfonyl indoles

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