Synthesis 2021; 53(07): 1262-1270
Straightforward Synthesis of Succinimide-Fused Pyrrolizidines by A Three-Component Reaction of α-Diketone, Amino Acid, and Maleimide
Peng Shen
a
Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, Zhejiang, P. R. of China
,
Yeting Guo
a
Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, Zhejiang, P. R. of China
,
Jian Wei
b
The State Key Laboratory of Chemical Oncogenomics, Shenzhen Graduate School of Peking University, Shenzhen 518055, P. R. of China
,
a
Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, Zhejiang, P. R. of China
,
Hongbin Zhai∗
b
The State Key Laboratory of Chemical Oncogenomics, Shenzhen Graduate School of Peking University, Shenzhen 518055, P. R. of China
,
Yufen Zhao
a
Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, Zhejiang, P. R. of China
› Author Affiliations We thank the National Natural Science Foundation of China (no. 22001137), the Science and Technology Planning Project of Guangdong Province (no. 2017B030314002), and the Natural Science Foundation of Zhejiang Province (no. LQ20B020003) for financial support.
Abstract
An efficient, one-pot, three-component [3+2] cycloaddition reaction of azomethine ylide obtained from α-dicarbonyl compounds (cyclic and acyclic diketone or keto ester) and amino acids with maleimides under catalyst-free conditions has been developed. This cascade protocol shows high efficiency and remarkable functional group tolerance, and the ubiquitous succinimide-fused pyrrolizidines with a highly compact and strained scaffold were obtained with high yield and excellent diastereoselectivity. Furthermore, this novel and atom-economical strategy could be performed on a gram scale with comparable reaction efficiency.
Key words
[3+2] cycloaddition -
multicomponent reaction -
α-diketone -
maleimide -
succinimide-fused pyrrolizidine
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706608.
Supporting Information
Publication History
Received: 22 October 2020
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
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14 CCDC 2032035 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
