Synthesis of 2-Methylindoline- and 2-Methyl-1,2,3,4-tetrahydroquinoline-Derived Phosphoramidites and Their Applications in Iridium-Catalyzed Allylic Alkylation of Indoles

被引：82
|
作者：
Liu, Wen-Bo [1 ]
He, Hu [1 ]
Dai, Li-Xin [1 ]
You, Shu-Li [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2009年 / 12期
关键词：
allylic alkylation; Friedel-Crafts reaction; indoles; iridium; phosphoramidites; ASYMMETRIC HYDROGENATION; ENANTIOSELECTIVE ALLYLATION; KINETIC RESOLUTION; 2,4-DISUBSTITUTED CYCLOPENTENONES; PHOSPHORUS AMIDITES; SUBSTITUTION; LIGANDS; COMPLEX; QUINOLINES; AMINATION;
D O I：
10.1055/s-0029-1216823
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of novel phosphoramidite ligands were synthesized from enantiopure BINOL and 2-methylindoline or 2-methyl-1,2,3,4-tetrahydroquinoline. These ligands were found to be efficient in iridium-catalyzed Friedel-Crafts reaction of indoles with allylic carbonates, affording branched products with high regio- and enantioselectivities. Strikingly, these ligands were demonstrated to be superior to the Feringa ligands when the ortho-substituted cinnamyl carbonates were used.
引用
收藏
页码：2076 / 2082
页数：7
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