Highly Efficient and Diastereoselective Construction of Trifluoromethyl‐Containing Spiro[pyrrolidin‐3, 2′‐oxindole] by a Catalyst‐free Mutually Activated [3+2] Cycloaddition Reaction. Issue 40 (19th June 2018)

• Record Type: Journal Article
• Authors: Gui, Hou‐Ze; Gao, Yu‐Ning; Wei, Yin; Shi, Min
• Is Part Of: Chemistry. Volume 24:Issue 40(2018)
• Page Start: 10038
• Page End: 10043
• Publication Date: 2018-06-19
• Subjects: catalyst-free -- cycloaddition -- mutual activation -- self-catalyzed -- spiro compounds; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201801971
• Languages: English
• ISSNs: 0947-6539

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 p K a 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 : A catalyst‐free, self‐catalyzed and highly diastereoselective synthesis of spiro[pyrrolidin‐3, 2′‐oxindole] through mutual activation of isatin‐derived α‐(trifluoromethyl)imines and vinylpyridines has been developed that provides the desired products in good yields.