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Decarboxylative, Diastereoselective and exo-Selective 1,3-Dipolar Cycloaddition for Diversity-Oriented Construction of Structural Spiro[Butyrolactone–Pyrrolidine–Chromanone] Hybrids

Authors :
Lei Zhang
Dong-Gui Guo
Xiong-Li Liu
Xiao-Xue Han
Li Zheng
Min Zhang
Source :
Synlett. 32:1447-1452
Publication Year :
2021
Publisher :
Georg Thieme Verlag KG, 2021.

Abstract

Inspired by the chemistry and biology of butyrolactones, pyrrolidines, and chromanones, we successfully developed a simple domino 1,3-dipolar cycloaddition of homoserine-lactone-derived azomethine ylides for the construction of biologically important spiro[butyrolactone–pyrrolidine–chromanone] hybrids in the presence of Et3N as a catalyst under mild conditions. The reaction is based on the application of carboxylic-acid-activated chromones as dienophiles, followed by a decarboxylation process. This reaction displayed good substrate tolerance and gave the desired products in moderate to good yields with high diastereoselectivities (up to 85% yield and >20:1 diastereomeric ratio) via an exo-transition state. This is the first example of an introduction of a chromanone moiety into a spiro[butyrolactone-pyrrolidine] framework, which might be valuable in medicinal chemistry.

Details

ISSN :
14372096 and 09365214
Volume :
32
Database :
OpenAIRE
Journal :
Synlett
Accession number :
edsair.doi...........dd5d6a7873ad33045426e7ef155a838b
Full Text :
https://doi.org/10.1055/a-1535-8891