Journal
TETRAHEDRON
Volume 70, Issue 15, Pages 2537-2545Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.02.050
Keywords
1,3-Dipolar cycloaddition; Dimethylaminopyridine; Pyridinium N-ylide; Spirooxindole
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Funding
- National Natural Science Foundation of China [21172189]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
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The cycloaddition reactions of 4-dimethylamino-1-alkoxycarbonylmethylpyridinium bromides with various 2-oxoindolin-3-ylidene derivatives in ethanol in the presence of triethylamine afforded the unprecedented dispirocyclopentanebisoxindole derivatives in good yields and in high diastereoselectivity. Under similar reaction conditions, the reactions of 1-alkoxycarbonylmethylpyridinium bromides with 3-phenacylideneoxindoles only resulted in 4-oxo-3-(2-oxoindolin-3-ylidene)-4-arylbutanoates. The stereochemistry of the complex spirooxindoles was established by H-1 NMR data and single crystal structures. (C) 2014 Elsevier Ltd. All rights reserved.
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