C-H Oxidation/Michael Addition/Cyclization Cascade for Enantioselective Synthesis of Functionalized 2-Amino-4H-chromenes

被引：80

作者：

Wu, Bo ^{[1
]}

Gao, Xiang ^{[1
]}

Yan, Zhong ^{[1
]}

Chen, Mu-Wang ^{[1
]}

Zhou, Yong-Gui ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

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

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 24期

基金：

中国国家自然科学基金;

关键词：

ORTHO-QUINONE METHIDES; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; IN-SITU; ACTIVATION STRATEGY; APOPTOSIS INDUCERS; G-QUADRUPLEX; ACID; CYCLIZATION; DISCOVERY;

D O I：

10.1021/acs.orglett.5b03148

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A streamlined method for the enantioselective synthesis of 2-amino-4H-chromenes from readily available 2-alkyl-substituted phenols and active methylene compounds bearing a cyano group with up to 97% ee is presented. This reaction is a cascade procedure including manganese dioxide mediated CH oxidation for the generation of o-quinone methides and bifunctional squaramide-catalyzed Michael addition/cyclization.

引用

页码：6134 / 6137

页数：4

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