Three‐component 1,3‐dipolar cycloaddition reactions in synthesis of spiro[pyrrolidine‐2,3′‐oxindoline] derivatives

Regio‐ and stereospecific syntheses of several spiro[pyrrolidine2,3′‐oxindole] derivatives by cycloaddition trapping of azomethine ylides generated in situ, via decarboxylative condensation of isatin with α‐amino acids or by reaction of secondary amines with isatin, are reported. 2,6‐Dibenzylidenecyclohexanone, 2‐arylidene‐1‐tetralone, and arylidenemalononitrile derivatives have been efficiently used as trapping dipolarophiles. The regio‐ and stereochemistry of the additions are controlled by both frontier orbital and steric interactions. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:324–329, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10038