Asymmetric Synthesis of Triaryl-Substituted Chromans with Multiple Stereogenic Centers by [4+2] Cycloaddition Reaction

被引：17

作者：

Zhang, Heng ^{[1
]}

Liu, Guofeng ^{[1
]}

Guan, Xukai ^{[1
]}

Gao, Jigang ^{[1
]}

Qin, Xiangshuo ^{[1
]}

Jiang, Guofeng ^{[1
]}

Sun, Dongyang ^{[1
]}

Zhang, Guangliang ^{[1
]}

Zhang, Suoqin ^{[1
]}

机构：

[1] Jilin Univ, Coll Chem, 2699 Qianjin St, Changchun 130012, Jilin, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 43期

基金：

中国国家自然科学基金;

关键词：

Enantioselective; Chromans; O-Quinone Metheides; 1-Styrylnaphthols; Chiral Imidodiphosphoric Acids; ORTHO-QUINONE METHIDES; FRIEDEL-CRAFTS REACTIONS; AXIALLY CHIRAL BISPHOSPHORYLIMIDES; O-HYDROXYBENZYL ALCOHOLS; IN-SITU; ENANTIOSELECTIVE SYNTHESIS; POVAROV REACTION; ACID; CONSTRUCTION; INDOLES;

D O I：

10.1002/ejoc.201901286

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric synthesis of triaryl-substituted chromans with multiple adjacent stereogenic centers is described here. [4+2] formal oxa-Diels-Alder cycloaddition of 1-styrylnaphthols and in-situ-generated o-quinone metheides could proceed smoothly in the presence of H-8-BINOL-type chiral imidodiphosphoric acids as catalyst. This method provides an efficient strategy to construct chiral chroman frameworks in high yields (up to 93 %) with excellent stereoselectivities (> 19:1 dr.) and enantioselectivities (up to 99 % ee).

引用

页码：7264 / 7268

页数：5

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