Journal
ORGANIC LETTERS
Volume 10, Issue 18, Pages 4009-4012Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol8015176
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Funding
- Merck Summer Fellowship
- Bristol-Myers Squibb Graduate Fellowship in Synthetic Organic Chemistry
- Fonds Quebecois de la Recherche sur la Nature et les Technologies
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The oxidation of 2-aryl tryptamines followed by a stereoselective rearrangement provides a versatile strategy for the synthesis of C3-quaternary oxindoles bearing a C3-aryl group. Treatment of optically active 2-aryl hydroxyindolenines with scandium trifluoromethanesulfonate in toluene at 110 degrees C leads to complete and stereoselective isomerization to the corresponding C3-aryl oxindoles which represent versatile intermediates for the synthesis of C3a-aryl hexahydropyrroloindoles.
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