Direct synthesis of fluorene-based spirolactones through a BF3-promoted spiroannulation of α-keto acids and o-alkynylbiaryls

Qingting Song; Zhen Zhang; Xiaoyu Xie; Guang-Zhu Ding; Pinhua Li; Lei Wang; Tao Miao

doi:10.1039/D2QO01523D

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Direct synthesis of fluorene-based spirolactones through a BF₃-promoted spiroannulation of α-keto acids and o-alkynylbiaryls†

Qingting Song,^a Zhen Zhang,^a Xiaoyu Xie,^a Guang-Zhu Ding,

*^a Pinhua Li,

^a Lei Wang

^abc and Tao Miao

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Green and Precise Synthetic Chemistry and Application, Ministry of Education, Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China
E-mail: taomiao@chnu.edu.cn, dinggz@chnu.edu.cn

^b Advanced Research Institute and Department of Chemistry, Taizhou University, Taizhou, Zhejiang 318000, P. R. China

^c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P R China

Abstract

A novel and practical approach to substituted fluorene-based spirolactones has been described via an efficient BF₃-promoted spiroannulation of α-keto acids and o-alkynyl biaryls. This metal-free cascade reaction proceeds smoothly at room temperature, and provides a wide range of structurally diverse products in good to excellent yields under mild conditions.

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/D2QO01523D
Article type: Research Article
Submitted: 24 Sep 2022
Accepted: 20 Nov 2022
First published: 24 Nov 2022

Download Citation

Org. Chem. Front., 2023,10, 363-368

Permissions

Request permissions

Direct synthesis of fluorene-based spirolactones through a BF₃-promoted spiroannulation of α-keto acids and o-alkynylbiaryls

Q. Song, Z. Zhang, X. Xie, G. Ding, P. Li, L. Wang and T. Miao, Org. Chem. Front., 2023, 10, 363 DOI: 10.1039/D2QO01523D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic Chemistry Frontiers