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Synlett 2021; 32(14): 1447-1452
DOI: 10.1055/a-1535-8891
DOI: 10.1055/a-1535-8891
letter
Decarboxylative, Diastereoselective and exo-Selective 1,3-Dipolar Cycloaddition for Diversity-Oriented Construction of Structural Spiro[Butyrolactone–Pyrrolidine–Chromanone] Hybrids
Authors
We are grateful for the financial support from the NSFC (81760625 and 22061006) and Science and Technology Program of Guizhou Province ([2020]4Y205, [2020]1Z074, [2018]5781, and [2017]7295).
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.
Key words
1,3-dipolar cycloaddition - chromones - spiro compounds - azomethine ylides - pyrrolidines - lactonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1535-8891.
- Supporting Information (PDF)
Publication History
Received: 24 April 2021
Accepted after revision: 24 June 2021
Accepted Manuscript online:
24 June 2021
Article published online:
15 July 2021
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