Multigram Synthesis of a Chiral Substituted Indoline Via Copper-Catalyzed Alkene Aminooxygenation

被引:19
作者
Sequeira, Fatima C. [1 ]
Bovino, Michael T. [1 ]
Chipre, Anthony J. [1 ]
Chemler, Sherry R. [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
来源
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 10期
基金
美国国家卫生研究院;
关键词
indoline; aminooxygenation; copper-catalyzed; alkene; TEMPO;
D O I
10.1055/s-0031-1289762
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(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 (4R,5S)-di-Ph-box ligand and efficient separation of a monoallylaniline from its N,N-diallylaniline by-product by distillation under reduced pressure.
引用
收藏
页码:1481 / 1484
页数:4
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