Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 9, Pages 3148-3152Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510692
Keywords
asymmetric synthesis; heterocycles; hydrogen transfer; kinetic resolution; organocatalyst
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Funding
- MEXT, Japan
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A strategy for oxidative kinetic resolution of racemic indolines was developed, employing salicylaldehyde derivative as the pre-resolving reagent and chiral phosphoric acid as the catalyst. The iminium intermediate, formed by the condensation reaction of an enantiomer of indoline with salicylaldehyde derivative, was hydrogenated by the same enantiomer of indoline to afford another enantiomer of indoline by a self-redox mechanism. The oxidative kinetic resolution of 2-aryl-substituted indolines proceeded to give enantiomers in good yields with excellent enantioselectivities.
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