Chiral counteranion-directed silver-catalyzed asymmetric synthesis of 1,2-dihydroisoquinolines by Friedel-Crafts alkylation reactions

被引：31

作者：

Zhang, Jun-Wei ^{[1
,2
]}

Xu, Zhe ^{[2
]}

Gu, Qing ^{[2
]}

Shi, Xiao-Xin ^{[1
]}

Leng, Xue-Bing ^{[2
]}

You, Shu-Li ^{[1
,2
]}

机构：

[1] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2012年 / 68卷 / 26期

关键词：

Chiral counteranion; 1,2-Dihydroisoquinoline; Friedel-Crafts alkylation; Chiral sliver phosphate; Asymmetric synthesis; ENANTIOSELECTIVE BRONSTED ACID; PICTET-SPENGLER REACTIONS; TANDEM NUCLEOPHILIC-ADDITION; TRANSITION-METAL CATALYSIS; PLATELET-ACTIVATING-FACTOR; FORMAL TOTAL-SYNTHESIS; DNA-BINDING AGENTS; ONE-POT REACTION; BETA-PHENYLETHYLAMINES; COOPERATIVE CATALYSIS;

D O I：

10.1016/j.tet.2012.02.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of ortho-alkynylaryl aldimines and indoles catalyzed by a silver binol-derived phosphate was realized to afford a series of enantioenriched 1,2-dihydroisoquinolines in moderate to good yields and ee. An interesting phenomenon that highly enantioenriched products could be obtained from their lower ee form by silica gel column chromatography was observed, providing an easy access to the enantiopure form of the product. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5263 / 5268

页数：6

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