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Synthesis 2022; 54(02): 429-438
DOI: 10.1055/a-1625-9538
paper

A Catalyst-Free Synthesis of Fused Perfluoroalkylated 2,3-Dihydroisoxazoles via Oxa-Michael-Aldol Annulation

Wei Zhou‡
a   School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, P. R. of China
,
Lan Yao‡
b   Inspection Department, Shanghai Blood Center, Shanghai 200051, P. R. of China
,
Yongxiurong Liu
c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Lichun Shen
d   Qianweichang College, Shanghai University, Shanghai, 200444, P. R. of China
,
Jie Chen
c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Hongmei Deng
e   Laboratory for Microstructures, Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Min Shao
e   Laboratory for Microstructures, Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Hui Zhang∗
c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
e   Laboratory for Microstructures, Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Xiaojun Tang∗
c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Weiguo Cao∗
a   School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, P. R. of China
c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
f   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
› Author AffiliationsThe authors are grateful to the National Natural Science Foundation of China (Grant No. 21672138) for financial support.
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Abstract

A novel synthesis of fused perfluoroalkylated 2,3-dihydroisoxazoles is achieved via oxa-Michael-aldol annulation between perfluoroalk-2-ynoates and N-hydroxyimides. This method provides a convenient route for the synthesis of pyrrolidin-2-one-fused perfluoroalkylated 2,3-dihydroisoxazoles in yields of up to 97%. Diverse and pharmaceutically attractive polycyclic scaffolds can be obtained rapidly and efficiently under these mild, catalyst-free conditions.

Key words

dihydroisoxazoles - piperidin-2-ones - perfluoroalkylated - oxa-Michael-aldol annulation - catalyst-free conditions

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1625-9538.
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Publication History

Received: 03 August 2021

Accepted after revision: 31 August 2021

Accepted Manuscript online:
31 August 2021

Article published online:
17 September 2021

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