Issue 8, 2020
From the journal:

Organic Chemistry Frontiers

Construction of spirooxindole-fused spiropyrazolones containing contiguous three stereogenic centres via [3 + 2] annulation utilizing a ferrocene derived bifunctional phosphine catalyst†

Wenjun Luo,a   Bingxuan Shao,a   Jingyi Li,a   Xiao Xiao,a   Dingguo Song,a   Fei Ling ORCID logo a  and  Weihui Zhong ORCID logo *a  

* Corresponding authors

a Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
E-mail: weihuizhong@zjut.edu.cn

Abstract

A ferrocene-derived bifunctional phosphine-catalyzed enantioselective [3 + 2] annulation of γ-substituted allenoates with pyrazoloneyldiene oxindoles is investigated for the construction of spiro-cyclopentene-linked oxindole and pyrazolone compounds, which bear three consecutive stereocenters and two vicinal spiroquaternary chiral centers, in good chemical yields (up to 95%) with excellent regio-, diastereo- (dr > 19 : 1) and enantioselectivities (up to 98% ee).

Graphical abstract: Construction of spirooxindole-fused spiropyrazolones containing contiguous three stereogenic centres via [3 + 2] annulation utilizing a ferrocene derived bifunctional phosphine catalyst

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Article information

DOI
https://doi.org/10.1039/D0QO00140F
Article type
Research Article
Submitted
05 Feb 2020
Accepted
18 Mar 2020
First published
19 Mar 2020

Org. Chem. Front., 2020,7, 1016-1021

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Construction of spirooxindole-fused spiropyrazolones containing contiguous three stereogenic centres via [3 + 2] annulation utilizing a ferrocene derived bifunctional phosphine catalyst

W. Luo, B. Shao, J. Li, X. Xiao, D. Song, F. Ling and W. Zhong, Org. Chem. Front., 2020, 7, 1016 DOI: 10.1039/D0QO00140F

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