Enantioselective gold-catalyzed intermolecular [2 + 2]-cycloadditions of 3-styrylindoles with N-allenyl oxazolidinone

Haoxiang Hu; Yidong Wang; Deyun Qian; Zhan-Ming Zhang; Lu Liu; Junliang Zhang

doi:10.1039/C6QO00087H

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Enantioselective gold-catalyzed intermolecular [2 + 2]-cycloadditions of 3-styrylindoles with N-allenyl oxazolidinone†

Haoxiang Hu,^a Yidong Wang,^a Deyun Qian,^a Zhan-Ming Zhang,^a Lu Liu*^a and Junliang Zhang*^ab

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* Corresponding authors

^a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China
E-mail: lliu@chem.ecnu.edu.cn, jlzhang@chem.ecnu.edu.cn

^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, China

Abstract

The enantioselective intermolecular [2 + 2] cycloaddition of 3-styrylindoles with N-allenyl oxazolidinone has been achieved for the first time by the employment of a Xiang-Phos derived chiral gold-catalyst. The corresponding cycloadducts could be obtained in good yields (up to 95%) with up to 95% ee.

This article is part of the themed collections: HOT articles in Organic Chemistry Frontiers in 2016 and 2015 Emerging Investigators by OCF

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DOI: https://doi.org/10.1039/C6QO00087H
Article type: Research Article
Submitted: 03 mar 2016
Accepted: 18 apr 2016
First published: 20 apr 2016

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Org. Chem. Front., 2016,3, 759-763

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Enantioselective gold-catalyzed intermolecular [2 + 2]-cycloadditions of 3-styrylindoles with N-allenyl oxazolidinone

H. Hu, Y. Wang, D. Qian, Z. Zhang, L. Liu and J. Zhang, Org. Chem. Front., 2016, 3, 759 DOI: 10.1039/C6QO00087H

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Organic Chemistry Frontiers

Enantioselective gold-catalyzed intermolecular [2 + 2]-cycloadditions of 3-styrylindoles with N-allenyl oxazolidinone†

Abstract

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Enantioselective gold-catalyzed intermolecular [2 + 2]-cycloadditions of 3-styrylindoles with N-allenyl oxazolidinone

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