Copper(I)-catalyzed asymmetric [3 + 3] annulation involving aziridines to construct tetrahydro-β-carbolines

Chao Ye; Wu-Lin Yang; Yufei Zhai; Hua Deng; Xiaoyan Luo; Guoyin Kai; Wei-Ping Deng

doi:10.1039/D0QO00742K

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Copper(i)-catalyzed asymmetric [3 + 3] annulation involving aziridines to construct tetrahydro-β-carbolines†

Chao Ye,‡^b Wu-Lin Yang,

‡^ab Yufei Zhai,^a Hua Deng,^b Xiaoyan Luo,

*^b Guoyin Kai*^a and Wei-Ping Deng

^ab

Author affiliations

* Corresponding authors

^a College of Pharmacy, Zhejiang Chinese Medical University, Hangzhou 310053, Zhejiang, China
E-mail: kaiguoyin@163.com

^b Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
E-mail: xyluo@ecust.edu.cn

Abstract

A catalytic asymmetric [3 + 3] annulation of aziridines with substituted 2-vinylindoles was developed. The reaction proceeds through copper-catalyzed ring-opening of aziridines followed by base-promoted intramolecular aza-Michael addition in a one-pot process. This strategy provides an efficient method for the direct synthesis of 1,4-disubstituted tetrahydro-β-carbolines with generally high diastereo- and enantioselectivities (up to >20 : 1 dr, 96% ee).

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DOI: https://doi.org/10.1039/D0QO00742K
Article type: Research Article
Submitted: 23 Jun 2020
Accepted: 14 Sep 2020
First published: 17 Sep 2020

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Org. Chem. Front., 2020,7, 3393-3398

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Copper(I)-catalyzed asymmetric [3 + 3] annulation involving aziridines to construct tetrahydro-β-carbolines

C. Ye, W. Yang, Y. Zhai, H. Deng, X. Luo, G. Kai and W. Deng, Org. Chem. Front., 2020, 7, 3393 DOI: 10.1039/D0QO00742K

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Organic Chemistry Frontiers

Copper(i)-catalyzed asymmetric [3 + 3] annulation involving aziridines to construct tetrahydro-β-carbolines†

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Copper(I)-catalyzed asymmetric [3 + 3] annulation involving aziridines to construct tetrahydro-β-carbolines

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