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Synthesis 2022; 54(07): 1870-1876
DOI: 10.1055/s-0041-1737817
DOI: 10.1055/s-0041-1737817
paper
Diastereoselective Synthesis of Spirocyclopentene-Indanediones from Isocyanides, Acetylenic Esters, and NH-Acidic Compounds
We are grateful to the Research Council of Tarbiat Modares University for support of this work.
Abstract
A diastereoselective synthesis of spirocyclopentene-1H-indene-1,3(2H)-diones through a three-component reaction of alkyl isocyanides, dialkyl acetylenedicarboxylates, and 2-(alkylamino)-2-(1,3-dioxo-1H-inden-2(3H)-ylidene)acetonitriles is described. This reaction forms two stereogenic centers with remarkable diastereoselectivity. The crystal structure of a typical product has been determined by X-ray diffraction.
Key words
spriro compounds - diastereoselective synthesis - alkyl isocyanides - Huisgen zwitterion - ninhydrinSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737817.
- Supporting Information
Publication History
Received: 16 May 2021
Accepted after revision: 15 November 2021
Article published online:
21 January 2022
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