Organocatalytic diastereo- and atropo-selective construction of eight-membered bridged (hetero)biaryls via asymmetric intramolecular [3 + 2] cycloaddition

Yue Wang; Yue Huang; Xiaoze Bao; Xingfu Wei; Shiqiang Wei; Jingping Qu; Baomin Wang

doi:10.1039/D4SC01892C

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Organocatalytic diastereo- and atropo-selective construction of eight-membered bridged (hetero)biaryls via asymmetric intramolecular [3 + 2] cycloaddition†

Yue Wang,^a Yue Huang,^a Xiaoze Bao,

^b Xingfu Wei,^a Shiqiang Wei,^a Jingping Qu

^a and Baomin Wang

*^a

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* Corresponding authors

^a Department of Pharmaceutical Engineering, State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. China
E-mail: bmwang@dlut.edu.cn

^b College of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. China

Abstract

An unprecedented and straightforward route for the asymmetric construction of privileged atroposelective bridged (hetero)biaryl eight-membered scaffolds has been accomplished through chiral phosphoric acid catalyzed asymmetric intramolecular [3 + 2] cycloaddition of innovative (hetero)biaryl aldehydes with 3-aminooxindole hydrochlorides. A class of eight-membered bridged (hetero)biaryl lactones fused to spiro[pyrrolidine-oxindole] derivatives, possessing both chiral C–C/C–N axes and multiple contiguous stereocenters, were obtained in good yields with excellent enantioselectivities and diastereoselectivities in one step through this direct strategy. In addition, the good scalability and derivatization of the title compounds demonstrated their synthetic utility.

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DOI: https://doi.org/10.1039/D4SC01892C
Article type: Edge Article
Submitted: 21 Mar 2024
Accepted: 07 May 2024
First published: 07 May 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2024, Advance Article

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Organocatalytic diastereo- and atropo-selective construction of eight-membered bridged (hetero)biaryls via asymmetric intramolecular [3 + 2] cycloaddition

Y. Wang, Y. Huang, X. Bao, X. Wei, S. Wei, J. Qu and B. Wang, Chem. Sci., 2024, Advance Article , DOI: 10.1039/D4SC01892C

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Chemical Science

Organocatalytic diastereo- and atropo-selective construction of eight-membered bridged (hetero)biaryls via asymmetric intramolecular [3 + 2] cycloaddition†

Abstract

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Organocatalytic diastereo- and atropo-selective construction of eight-membered bridged (hetero)biaryls via asymmetric intramolecular [3 + 2] cycloaddition

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