Catalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-Oxindoles

No more double trouble: The competing double‐addition pathway was suppressed when chiral scandium(III) and indium(III) complexes were used to catalyze the addition of indoles and other π nucleophiles to N‐alkylated and unprotected isatins (see picture). The resulting biologically relevant substitute...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2010-01, Vol.49 (4), p.744-747
Main Authors: Hanhan, Nadine V, Sahin, Aziza H, Chang, Toby W, Fettinger, James C, Franz, Annaliese K
Format: Article
Language:English
Subjects:
asymmetric catalysis
Catalysis
Crystallography, X-Ray
heterocycles
indium
Indium - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Isatin - chemistry
Molecular Conformation
nucleophilic addition
scandium
Scandium - chemistry
Stereoisomerism
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Summary:No more double trouble: The competing double‐addition pathway was suppressed when chiral scandium(III) and indium(III) complexes were used to catalyze the addition of indoles and other π nucleophiles to N‐alkylated and unprotected isatins (see picture). The resulting biologically relevant substituted 3‐hydroxy‐2‐oxindoles were obtained in high yield with high enantioselectivity. Tf=trifluoromethanesulfonyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200904393