Enantioselective synthesis of substituted oxindoles and spirooxindoles with applications in drug discovery.
This review describes recent methods for the enantioselective synthesis of oxindoles and spirooxindoles, with a particular focus on scaffolds with applications in drug discovery. The synthetic challenge of the spiro-motif and the important biological activity of spirooxindoles continue to encourage the development of creative methods to access these important structures. Unique spirocycles often result from creative synthetic methods that would not typically be identified using classical synthetic disconnections. To establish the importance of asymmetric synthesis in the context of oxindole structures, recent examples are highlighted in which stereospecific binding and differential biological activity have been demonstrated based on the configuration at the 3-position. This review is organized by type of catalyst and synthetic strategy in order to compare traditional organometallic and Lewis acid methods with more recent organocatalytic methods. A section describing multicomponent and cascade reaction strategies is also included.
University of California Davis, Department of Chemistry, 1 Shields Avenue, Davis, CA 95616, USA.
Joseph J
JJ
Badillo
Nadine V
NV
Hanhan
Annaliese K
AK
Franz
D000818:Animals; D002384:Catalysis; D003500:Cyclization; D055808:Drug Discovery / Q000379:methods*; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole