Asymmetric Cycloaddition of ortho-Hydroxyphenyl-Substituted para-Quinone Methides and Enamides Catalyzed by Chiral Phosphoric Acid

被引：41

作者：

Yang, Guo-Hui ^{[1
]}

Zhao, Qun ^{[1
]}

Zhang, Zhi-Pei ^{[1
]}

Zheng, Han-Liang ^{[1
]}

Chen, Li ^{[1
]}

Li, Xin ^{[1
]}

机构：

[1] Nankai Univ, State Key Lab Elementoorgan Chem, Coll Chem, Tianjin 300071, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 12期

关键词：

RAUHUT-CURRIER REACTION; BETA-ALKYNYL KETONES; DIELS-ALDER REACTION; 1,6-CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; CHROMANS BEARING; EXPEDIENT ACCESS; 4+1 ANNULATION; DERIVATIVES; DRUG;

D O I：

10.1021/acs.joc.9b00749

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A BINOL-based chiral phosphoric acid was employed as an efficient catalyst in enantioselective cycloaddition of ortho-hydroxyphenyl-substituted para-quinone methides and enamides, which gave rise to acetamido-substituted tetrahydroxanthenes with three adjacent stereogenic centers in high yields (up to 99%) and excellent stereoselectivities (up to >99:1 diastereomeric ratio and up to 98% ee).

引用

页码：7883 / 7893

页数：11

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