Highly enantioselective Friedel-Crafts alkylation of indole and pyrrole with β,γ-unsaturated α-ketoester catalyzed by chiral dicationic palladium complex

被引：34

作者：

Aikawa, Kohsuke ^{[1
]}

Honda, Kazuya ^{[1
]}

Mimura, Shunsuke ^{[1
]}

Mikami, Koichi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 50期

基金：

日本科学技术振兴机构;

关键词：

Friedel-Crafts alkylation; Lewis acid; Indole; Pyrrole; Ene reaction; BIS(OXAZOLINYL)PYRIDINE-SCANDIUM(III) TRIFLATE COMPLEXES; C-H BONDS; CONJUGATE ADDITION; ACID CATALYSIS; ASYMMETRIC-SYNTHESIS; AROMATIC-AMINES; PHOSPHORIC-ACID; HYDROXY ENONES; ENE REACTION; DERIVATIVES;

D O I：

10.1016/j.tetlet.2011.09.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral dicationic Pd complexes, bearing sterically demanding diphosphine ligands as Lewis acid catalysts, are shown to catalyze the asymmetric Friedel-Crafts (F-C) alkylations of indoles and pyrroles with beta,gamma-unsaturated alpha-ketoesters, to provide the F-C alkylation products with benzylic stereocenters in high yields and enantioselectivities. The reactive chelated structure, formed by the chiral dicationic Pd complex and the electrophile, would be important to gain a high level of asymmetric induction in the F-C alkylation. The F-C products can be readily functionalized to give alpha-hydroxy esters via catalytic asymmetric ene sequences. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6682 / 6686

页数：5

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