Highly enantioselective Friedel-Crafts alkylation of indole with electron deficient trans-β-nitroalkenes using Zn(II)-oxazoline-imidazoline catalysts

被引：38

作者：

Islam, Mohammad Shahidul ^{[1
]}

Al Majid, Abdullah M. A. ^{[1
]}

Al-Othman, Zeid Abdullah ^{[1
]}

Barakat, Assem ^{[1
]}

机构：

[1] King Saud Univ, Dept Chem, Fac Sci, Riyadh 11451, Saudi Arabia

来源：

TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 03期

关键词：

CONJUGATE ADDITION; BIS(OXAZOLINE) LIGANDS; STEREOSELECTIVE ALKYLATION; DIALKYLZINC REAGENTS; CARBONYL-COMPOUNDS; MICHAEL-ADDITIONS; CROSS-COUPLINGS; ALPHA; MALONATE; NITROOLEFINS;

D O I：

10.1016/j.tetasy.2013.11.018

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The catalytic asymmetric Friedel-Crafts alkylation of indole with trans-beta-nitroolefins has been developed via the catalysis of Zn(II)-oxazoline-imidazoline complexes. The reaction furnished nitroalkylated indoles in excellent yields (up to 95%) and with high enantioselectivities (up to 99% ee). The effects of solvent, temperature, the metal-triflate, and the ligand structure on the reaction are discussed. The substrates of the reaction can be substituted aromatic nitroolifins. The higher reactivity and enantioselectivity of the reaction could be due to the activation and asymmetric induction of chiral Lewis acids coordinated by the nitroolefin through a 1,3-metal bonded intermediate. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：245 / 251

页数：7

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