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手性磷酸催化的邻羟基苯基取代对苯醌甲基化物与烯酰胺的不对称环加成反应

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

作者信息

Yang Guo-Hui, Zhao Qun, Zhang Zhi-Pei, Zheng Han-Liang, Chen Li, Li Xin

机构信息

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry , Nankai University , Tianjin 300071 , China.

出版信息

J Org Chem. 2019 Jun 21;84(12):7883-7893. doi: 10.1021/acs.joc.9b00749. Epub 2019 Jun 7.

DOI:10.1021/acs.joc.9b00749
PMID:31134809
Abstract

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).

摘要

一种基于联萘酚的手性磷酸被用作邻羟基苯基取代对醌甲基化物与烯酰胺对映选择性环加成反应的高效催化剂,该反应以高产率(高达99%)和优异的立体选择性(高达>99:1的非对映体比例和高达98%的对映体过量)生成具有三个相邻手性中心的乙酰氨基取代四氢呫吨。

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引用本文的文献

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Organocatalytic enantioselective conjugate addition of 2-naphthols to -hydroxyphenyl substituted -quinone methides: access to unsymmetrical triarylmethanes.有机催化2-萘酚对β-羟基苯基取代的α-醌甲基化物的对映选择性共轭加成:通往不对称三芳基甲烷的途径。
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2
Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives [4 + 2] Annulation of -Tosylaminophenyl-Substituted Quinone Methides and Cyanoalkenes.四氢喹啉衍生物的高非对映选择性合成:对甲苯磺酰氨基苯基取代的醌甲基化物与氰基烯烃的[4 + 2]环化反应
Front Chem. 2021 Nov 3;9:764866. doi: 10.3389/fchem.2021.764866. eCollection 2021.