In:
Molecules, MDPI AG, Vol. 28, No. 14 ( 2023-07-13), p. 5372-
Abstract:
In this research, a metal-free diastereoselective formal 1,3-dipolar cycloaddition of N-2,2,2-trifluoroethylisatin ketimines and cyclopentene-1,3-diones which can efficiently lead to the desymmetrization of cyclopentene-1,3-diones is developed. With the developed protocol, a series of tetracyclic spirooxindoles containing pyrrolidine and cyclopentane subunits can be smoothly obtained with good results (up to 99% yield and 91:9 dr). Furthermore, the methodology can be extended to trifluoromethyl-substituted iminomalonate, and the corresponding formal [3+2] cycloaddition reaction affords bicyclic heterocycles containing fused pyrrolidine and cyclopentane moieties in moderate yields with 〉 20:1 dr. The synthetic potential of the methodology is demonstrated by the scale-up experiment and by versatile transformations of the products.
Type of Medium:
Online Resource
ISSN:
1420-3049
DOI:
10.3390/molecules28145372
Language:
English
Publisher:
MDPI AG
Publication Date:
2023
detail.hit.zdb_id:
2008644-1
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