Issue 17, 2021
From the journal:

Organic Chemistry Frontiers

Intramolecular Alder-ene cycloisomerization of cyclopropenes with alkenes to access spirocycles†

Peng Fan,a   Tian-Tian Liu,b   Hong-Yu Qu,a   Peng Tao,a   Chun-Xia Liu,a   Xiao-Qian Liu,a   Mei-Hua Shen, ORCID logo a   Xiaoguang Bao ORCID logo *b  and  Hua-Dong Xu ORCID logo *a  

* Corresponding authors

a Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Pharmacy, Changzhou University, Changzhou, Jiangsu Province 213164, China
E-mail: hdxu@cczu.edu.cn

b College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou Industrial Park, Suzhou, Jiangsu 215123, China
E-mail: xgbao@suda.edu.cn

Abstract

Cyclopropenes carrying an alkene moiety undergo a stereoselective Alder-ene cycloisomerization under thermal conditions. Diverse functionalized (hetero)spiro[2.4]heptanes are obtained with excellent trans diastereoselectivity. According to computational studies, this thermal process takes place via transition state TS(E-exo) or TS(Z-endo) if the former is not available.

Graphical abstract: Intramolecular Alder-ene cycloisomerization of cyclopropenes with alkenes to access spirocycles

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Article information

DOI
https://doi.org/10.1039/D1QO00299F
Article type
Research Article
Submitted
20 Feb 2021
Accepted
20 Jun 2021
First published
23 Jun 2021

Org. Chem. Front., 2021,8, 4799-4804

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Intramolecular Alder-ene cycloisomerization of cyclopropenes with alkenes to access spirocycles

P. Fan, T. Liu, H. Qu, P. Tao, C. Liu, X. Liu, M. Shen, X. Bao and H. Xu, Org. Chem. Front., 2021, 8, 4799 DOI: 10.1039/D1QO00299F

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