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Synthesis 2021; 53(07): 1262-1270
DOI: 10.1055/s-0040-1706608
DOI: 10.1055/s-0040-1706608
paper
Straightforward Synthesis of Succinimide-Fused Pyrrolizidines by A Three-Component Reaction of α-Diketone, Amino Acid, and Maleimide
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 pyrrolizidineSupporting 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
Accepted after revision: 24 October 2020
Article published online:
03 December 2020
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For 1,3-dipolar cycloaddition of isatin, see:
For 1,3-dipolar cycloaddition of proline, see: