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

被引：89

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

共 78 条

[1] Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile [J].

Adili, Alafate ;

Tao, Zhong-Lin ;

Chen, Dian-Feng ;

Han, Zhi-Yong .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (08) :2247-2250

[2] Asymmetric Cycloadditions of o-Quinone Methides Employing Chiral Ammonium Fluoride Precatalysts [J].

Alden-Danforth, Ethan ;

Scerba, Michael T. ;

Lectka, Thomas .

ORGANIC LETTERS, 2008, 10 (21) :4951-4953

[3] Synthesis and chemistry of quinone methide models for the anthracycline antitumor antibiotics [J].

Angle, SR ;

Rainier, JD ;

Woytowicz, C .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5884-5892

[4] SYNTHESIS AND CHEMISTRY OF A QUINONE METHIDE MODEL FOR ANTHRACYCLINE ANTITUMOR ANTIBIOTICS [J].

ANGLE, SR ;

YANG, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4524-4528

[5]

Arnouri H., 2002, ACCOUNTS CHEM RES, V35, P501

[6] The Domestication of ortho-Quinone Methides [J].

Bai, Wen-Ju ;

David, Jonathan G. ;

Feng, Zhen-Gao ;

Weaver, Marisa G. ;

Wu, Kun-Liang ;

Pettus, Thomas R. R. .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (12) :3655-3664

[7] Quinone Methides: Photochemical Generation and its Application in Biomedicine [J].

Basaric, Nikola ;

Mlinaric-Majerski, Kata ;

Kralj, Marijeta .

CURRENT ORGANIC CHEMISTRY, 2014, 18 (01) :3-18

[8] A Short Formal Total Synthesis of Strychnine with a Samarium Diiodide Induced Cascade Reaction as the Key Step [J].

Beemelmanns, Christine ;

Reissig, Hans-Ulrich .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (43) :8021-8025

[9] Mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-quinone methide [J].

Bishop, Lee M. ;

Winkler, Michael ;

Houk, Kendall N. ;

Bergman, Robert G. ;

Trauner, Dirk .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (18) :5405-5408

[10] ORTHO QUINONE METHIDES .2. TRAPPING WITH PRODUCTION OF CHROMANS [J].

BOLON, DA .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) :3666-&

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