Asymmetric organocatalytic (3 + 2) annulation of propargylic alcohols with indolylnaphthalenols: synergistic construction of axial and central chirality

Yan Xia; Meiwen Liu; Chenxiao Qian; Pengfei Li; Mingxin Dong; Wenjun Li

doi:10.1039/D2QO01625G

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Asymmetric organocatalytic (3 + 2) annulation of propargylic alcohols with indolylnaphthalenols: synergistic construction of axial and central chirality†

Yan Xia,‡^a Meiwen Liu,‡^b Chenxiao Qian,^b Pengfei Li,

*^b Mingxin Dong

*^a and Wenjun Li

*^a

Author affiliations

* Corresponding authors

^a Department of Medicinal Chemistry, School of Pharmacy, Qingdao University, Qingdao, Shandong, China
E-mail: mxdong64@qdu.edu.cn, liwj@qdu.edu.cn

^b Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, Southern University of Science and Technology, Shenzhen, Guangdong, China
E-mail: lipf@sustech.edu.cn, flyli1980@gmail.com

Abstract

Organocatalytic enantioselective construction of chiral spiro N,N-acetal carbon stereocenters and axially chiral 3-arylindoles has been achieved via a chiral phosphoric acid (CPA)-catalyzed (3 + 2) annulation of α-(3-isoindolinonyl) propargylic alcohols with 1-(3-indolyl)naphthalen-2-ols, affording a broad scope of pyrrolo[1,2-a]indoles bearing both enantioenriched spiro isoindolinone-indoline and atropisomeric naphthalenol frameworks. Based on control experiments and our previous work, a possible mechanism was proposed accordingly.

This article is part of the themed collection: 2023 Organic Chemistry Frontiers HOT articles

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DOI: https://doi.org/10.1039/D2QO01625G
Article type: Research Article
Submitted: 14 Oct 2022
Accepted: 08 Nov 2022
First published: 14 Nov 2022

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Org. Chem. Front., 2023,10, 30-34

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Asymmetric organocatalytic (3 + 2) annulation of propargylic alcohols with indolylnaphthalenols: synergistic construction of axial and central chirality

Y. Xia, M. Liu, C. Qian, P. Li, M. Dong and W. Li, Org. Chem. Front., 2023, 10, 30 DOI: 10.1039/D2QO01625G

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Organic Chemistry Frontiers

Asymmetric organocatalytic (3 + 2) annulation of propargylic alcohols with indolylnaphthalenols: synergistic construction of axial and central chirality†

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Asymmetric organocatalytic (3 + 2) annulation of propargylic alcohols with indolylnaphthalenols: synergistic construction of axial and central chirality

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