Multigram Synthesis of a Chiral Substituted Indoline Via Copper-Catalyzed Alkene Aminooxygenation
2012; Thieme Medical Publishers (Germany); Volume: 44; Issue: 10 Linguagem: Inglês
10.1055/s-0031-1289762
ISSN1437-210X
AutoresSherry R. Chemler, Fatima C. Sequeira, Michael T. Bovino, Anthony Chipre,
Tópico(s)Catalytic C–H Functionalization Methods
Resumo( S )-5-Fluoro-2-(2,2,6,6-tetramethylpiperidin-1-yloxymethyl)-1-tosylindoline, a 2-methyleneoxy-substituted chiral indoline, was synthesized on multigram scale using an efficient copper-catalyzed enantioselective intramolecular alkene aminooxygenation. The synthesis is accomplished in four steps and the indoline is obtained in 89% ee (>98% after one recrystallization). Other highlights include efficient gram-scale synthesis of the (4 R ,5 S )-di-Ph-box ligand and efficient separation of a monoallylaniline from its N , N -diallylaniline by-product by distillation under reduced pressure.
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