Organocatalytic Enantioselective Synthesis of 6-Aryl-5,6-dihydrophenanthridines by a Modified Pictet-Spengler Reaction of Biphenyl-2-amines and Aromatic Aldehydes

被引：12

作者：

Wang, Chaoceng ^{[1
]}

An, Dong ^{[1
]}

Guan, Xukai ^{[1
]}

Fan, Yansen ^{[1
]}

Liu, Guofeng ^{[1
]}

Zhang, Guangliang ^{[1
]}

Zhang, Suoqin ^{[1
]}

机构：

[1] Jilin Univ, Coll Chem, Changchun 130012, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 14期

基金：

中国国家自然科学基金;

关键词：

Asymmetric synthesis; Enantioselectivity; Fusedring systems; Nitrogen heterocycles; Organocatalysis; AXIALLY CHIRAL BISPHOSPHORYLIMIDES; FRIEDEL-CRAFTS REACTIONS; BRONSTED ACIDS; BENZOPHENANTHRIDINE ALKALOIDS; CYCLIZATION REACTIONS; ZANTHOXYLUM-NITIDUM; DERIVATIVES; DIHYDROCHELERYTHRINE; ARYLATION; PATHWAY;

D O I：

10.1002/ejoc.201700185

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward approach to the enantioselective synthesis of chiral 5,6-dihydrophenanthridines was developed. A series of chiral 6-aryl-5,6-dihydrophenanthridines were obtained through an organocatalytically modified Pictet-Spengler reaction of biphenyl-2-amines and aromatic aldehydes. In the reaction, H-8-BINOL-derived chiral imidodiphosphoric acid exhibited strong stereocontrolling and catalytic activities to afford the desired 6-aryl-5,6-dihydrophenanthridines in high yields (up to 98 %) with high enantioselectivities (up to 99 % ee).

引用

页码：1865 / 1869

页数：5

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