Movassaghi Mohammad, Schmidt Michael A, Ashenhurst James A
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 18-292, Cambridge, Massachusetts 02139, USA.
Org Lett. 2008 Sep 18;10(18):4009-12. doi: 10.1021/ol8015176. Epub 2008 Aug 23.
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.
2-芳基色胺的氧化反应，随后进行立体选择性重排，为合成带有C3-芳基的C3-季碳氧化吲哚提供了一种通用策略。在110℃下，将光学活性的2-芳基羟基吲哚啉与三氟甲磺酸钪在甲苯中反应，可导致其完全立体选择性异构化为相应的C3-芳基氧化吲哚，这些氧化吲哚是合成C3a-芳基六氢吡咯并吲哚的通用中间体。
