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Highly Efficient and Diastereoselective Construction of Trifluoromethyl‐Containing Spiro[pyrrolidin‐3,2′‐oxindole] by a Catalyst‐free Mutually Activated [3+2] Cycloaddition Reaction.
- Source :
- Chemistry - A European Journal; 7/17/2018, Vol. 24 Issue 40, p10038-10043, 6p
- Publication Year :
- 2018
-
Abstract
- Abstract: A catalyst‐free self‐catalyzed [3+2] cycloaddition reaction of isatin‐derived α‐(trifluoromethyl)imines with vinylpyridines is reported. The reaction offers a straightforward and atom‐economical procedure for the preparation of a series of 5′‐trifluoromethyl‐spiro[pyrrolidin‐3,2′‐oxindoles] in excellent yields and diastereoselectivities. The reaction mechanism has been investigated by control experiments, DFT calculation of pK<subscript>a</subscript> values and the kinetic profiles, revealing that this reaction featured the mutual activation between isatin‐derived α‐(trifluoromethyl)imines and vinylpyridine to generate the reactive species. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 09476539
- Volume :
- 24
- Issue :
- 40
- Database :
- Complementary Index
- Journal :
- Chemistry - A European Journal
- Publication Type :
- Academic Journal
- Accession number :
- 130795300
- Full Text :
- https://doi.org/10.1002/chem.201801971