Stereoselective oxidative rearrangement of 2-aryl tryptamine derivatives.
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.
Movassaghi
Mohammad
M
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 18-292, Cambridge, Massachusetts 02139, USA. movassag@mit.edu
Schmidt
Michael A
MA
Ashenhurst
James A
JA
D000470:Alkaloids / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D010084:Oxidation-Reduction; D000078183:Oxindoles; D011758:Pyrroles / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D014363:Tryptamines / Q000737:chemistry*
D000470:Alkaloids; D007211:Indoles; D000078183:Oxindoles; D011758:Pyrroles; D014363:Tryptamines; C022960:2-oxindole; C030820:tryptamine