A PPh3-catalyzed sequential annulation reaction to construct cyclopentane-fused dihydropyrazolone-pyrrolidinediones

Cheng Cheng; Xiaobin Sun; Zhiwei Miao

doi:10.1039/D0OB00815J

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A PPh₃-catalyzed sequential annulation reaction to construct cyclopentane-fused dihydropyrazolone-pyrrolidinediones†

Cheng Cheng,‡^a Xiaobin Sun ‡^a and Zhiwei Miao

*^ab

Author affiliations

* Corresponding authors

^a State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Weijin Road 94, Tianjin 300071, China
E-mail: miaozhiwei@nankai.edu.cn

^b Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China

Abstract

A PPh₃-catalyzed sequential cycloaddition of maleimides with unsaturated pyrazolones has been developed. This protocol provides a simple and practical strategy for the construction of dispirocyclopentyl-[dihydropyrazolone-pyrrolidinedione] pyrrolidinedione skeletons containing five contiguous stereogenic centers, including two spiro-quaternary centers, with moderate yields (34–73%) and excellent diastereoselectivities (>20 : 1).

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D0OB00815J
Article type: Communication
Submitted: 20 Apr 2020
Accepted: 26 Jun 2020
First published: 07 Jul 2020

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Org. Biomol. Chem., 2020,18, 5577-5581

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A PPh₃-catalyzed sequential annulation reaction to construct cyclopentane-fused dihydropyrazolone-pyrrolidinediones

C. Cheng, X. Sun and Z. Miao, Org. Biomol. Chem., 2020, 18, 5577 DOI: 10.1039/D0OB00815J

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Organic & Biomolecular Chemistry