Synthesis of Functionalized Indoles with a Trifluoromethyl-Substituted Stereogenic Tertiary Carbon Atom Through an Enantioselective Friedel-Crafts Alkylation with β-Trifluoromethyl-α,β-enones

被引：68

作者：

Blay, Gonzalo ^{[1
]}

Fernandez, Isabel ^{[1
]}

Carmen Munoz, M. ^{[2
]}

Pedro, Jose R. ^{[1
]}

Vila, Carlos ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Valencia, Spain

[2] Univ Politecn Valencia, Ctr Tecnol Fis, Valencia 46022, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 30期

关键词：

alkylation; aromatic substitution; asymmetric catalysis; enones; fluorinated compounds; TRIFLUOROACETALDEHYDE ETHYL HEMIACETAL; C-H BONDS; NUCLEOPHILIC TRIFLUOROMETHYLATION; STEREOSELECTIVE ALKYLATION; CASCADE REACTIONS; SIMPLE ENONES; NITROALKENES; FLUORINE; REACTIVITY; ALKALOIDS;

D O I：

10.1002/chem.201000568

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral complexes of BINOL-based ligands with zirconium tert-butoxide catalyze the Friedel-Crafts alkylation reaction of indoles with beta-trifluoromethyl-alpha,beta-unsaturated ketones to give functionalized indoles with an asymmetric tertiary carbon center attached to a trifluoromethyl group. The reaction can be applied to a large number of substituted alpha-trifluoromethyl enones and substituted indoles. The expected products were obtained with good yields and ees of up to 99%.

引用

页码：9117 / 9122

页数：6

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