An Unexpected Inversion of Enantioselectivity in a Copper-Catalyzed Intramolecular Desymmetric Aryl C-N Coupling Reaction

被引：11

作者：

Liu, Jiangguang ^{[1
,2
]}

Yan, Jiajie ^{[1
,2
]}

Qin, Dongguang ^{[1
,2
,3
]}

Cai, Qian ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Guangzhou Inst Biomed, Guangzhou 510530, Guangdong, Peoples R China

[2] Chinese Acad Sci, Guangzhou Inst Hlth, Guangzhou 510530, Guangdong, Peoples R China

[3] ABA Chem Corp, Shanghai 200063, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2014年 / 46卷 / 14期

关键词：

asymmetric desymmetrization; indolines; copper catalysis; N-arylation; inversion; KINETIC RESOLUTION; ARYLATION REACTION; DERIVATIVES; CHEMISTRY; HYDROGENATION; AMINATION; PALLADIUM; PLATINUM; HALIDES; AMIDES;

D O I：

10.1055/s-0033-1338638

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective formation of indolines was achieved through desymmetrization of alpha,alpha-bis(2-iodobenzyl)glycines under the catalysis of copper(I) iodide and (2S, 3aS, 7aS)-octahydro-1H-indole-2-carboxylic acid. An unexpected inversion of enantioselectivity was observed when achiral additives such as 4-(N,N-dimethylamino)pyridine were added which work together with the ligand. The configuration-reversed products were obtained in moderate yields as well as moderate ee values.

引用

页码：1917 / 1923

页数：7

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