Asymmetric synthesis of spirofuro[2,3-b]azepine-5,3′-indoline derivatives via cycloisomerization/[4 + 3] annulation process under Au/N-heterocyclic carbene relay catalysis

Mengwei You; Yan Li; Xin Lv; Guodong Shen; Xiao Xiao; Liejin Zhou

doi:10.1039/D3QO00539A

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Asymmetric synthesis of spirofuro[2,3-b]azepine-5,3′-indoline derivatives via cycloisomerization/[4 + 3] annulation process under Au/N-heterocyclic carbene relay catalysis†

Mengwei You,‡^a Yan Li,‡^a Xin Lv,

*^a Guodong Shen,^b Xiao Xiao

^c and Liejin Zhou

*^a

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* Corresponding authors

^a Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Material Sciences, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China
E-mail: lvxin@zjnu.cn, ljzhou@zjnu.cn

^b School of Chemistry and Chemical Engineering, Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, Liaocheng University, Liaocheng 252059, China

^c Institute of Pharmaceutical Science and Technology, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China

Abstract

A variety of enantioenriched spirofuro[2,3-b]azepine-5,3′-indoline derivatives (dr > 20 : 1, up to 96% ee) were facilely synthesized through cycloisomerization/asymmetric formal [4 + 3] cycloaddition reactions of enyne-amides with isatin-derived enals under gold(I)/chiral N-heterocyclic carbene (NHC) relay catalysis. The method is practical and useful because of the convenient one-step procedure, high stereoselectivity, and good functional-group tolerance.

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DOI: https://doi.org/10.1039/D3QO00539A
Article type: Research Article
Submitted: 11 Apr 2023
Accepted: 01 Jun 2023
First published: 02 Jun 2023

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Org. Chem. Front., 2023,10, 3347-3352

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Asymmetric synthesis of spirofuro[2,3-b]azepine-5,3′-indoline derivatives via cycloisomerization/[4 + 3] annulation process under Au/N-heterocyclic carbene relay catalysis

M. You, Y. Li, X. Lv, G. Shen, X. Xiao and L. Zhou, Org. Chem. Front., 2023, 10, 3347 DOI: 10.1039/D3QO00539A

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Organic Chemistry Frontiers

Asymmetric synthesis of spirofuro[2,3-b]azepine-5,3′-indoline derivatives via cycloisomerization/[4 + 3] annulation process under Au/N-heterocyclic carbene relay catalysis†

Abstract

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Asymmetric synthesis of spirofuro[2,3-b]azepine-5,3′-indoline derivatives via cycloisomerization/[4 + 3] annulation process under Au/N-heterocyclic carbene relay catalysis

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