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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Stereoselective oxidative rearrangement of 2-aryl tryptamine derivatives
Mohammad Movassaghi1, Michael A Schmidt, James A Ashenhurst
1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 18-292, Cambridge, Massachusetts 02139, USA. movassag@mit.edu
Abstract:
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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