Phosphine-Catalyzed Enantioselective [4+2] Annulation of o-Quinone Methides with Allene Ketones

被引：86

作者：

Wang, Zhen ^{[1
,2
]}

Wang, Tianli ^{[2
]}

Yao, Weijun ^{[2
]}

Lu, Yixin ^{[2
,3
]}

机构：

[1] Chongqing Univ, Sch Pharmaceut Sci, Chongqing Key Lab Nat Prod Synth & Drug Res, Chongqing 401331, Peoples R China

[2] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

[3] Natl Univ Singapore, Suzhou Res Inst, Suzhou 215123, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 15期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC GAMMA-ADDITION; IN-SITU; FUNCTIONALIZED CYCLOPENTENES; DIASTEREOSELECTIVE SYNTHESIS; ACID; CYCLOADDITION; ALLENOATES; 2,3-BUTADIENOATES; CONSTRUCTION; ACTIVATION;

D O I：

10.1021/acs.orglett.7b01936

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A phosphine-catalyzed highly enantioselective [4 + 2] annulation between ortho-quinone methides and allene ketones has been developed. The reported method led to the formation of chromane derivatives in high yields and excellent enantioselectivity. This is the first time that ortho-quinone methides are employed in phosphine-mediated cyclization reactions.

引用

页码：4126 / 4129

页数：4

共 89 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] Synergistic Rhodium/Phosphoric Acid Catalysis for the Enantioselective Addition of Oxonium Ylides to ortho-Quinone Methides [J].

Alamsetti, Santosh Kumar ;

Spanka, Matthias ;

Schneider, Christoph .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (07) :2392-2396

[3] 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

[4] 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

[5] Natural Product Biosynthesis Inspired Concise and Stereoselective Synthesis of Benzopyrones and Related Scaffolds [J].

Baskar, Baburaj ;

Dakas, Pierre-Yves ;

Kumar, Kamal .

ORGANIC LETTERS, 2011, 13 (08) :1988-1991

[6] Catalytic Asymmetric Addition of Meldrum's Acid, Malononitrile, and 1,3-Dicarbonyls to ortho-Quinone Methides Generated In Situ Under Basic Conditions [J].

Caruana, Lorenzo ;

Mondatori, Martina ;

Corti, Vasco ;

Morales, Sara ;

Mazzanti, Andrea ;

Fochi, Mariafrancesca ;

Bernardi, Luca .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (16) :6037-6041

[7] Enantioselective Reactions of 2-Sulfonylalkyl Phenols with Allenic Esters: Dynamic Kinetic Resolution and [4+2] Cycloaddition Involving ortho-Quinone Methide Intermediates [J].

Chen, Ping ;

Wang, Kai ;

Guo, Wengang ;

Liu, Xianghui ;

Liu, Yan ;

Li, Can .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (13) :3689-3693

[8] Enantioselective [3+2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing α-amino acid [J].

Cowen, Bryan J. ;

Miller, Scott J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :10988-+

[9] Enantioselective catalysis and complexity generation from allenoates [J].

Cowen, Bryan J. ;

Miller, Scott J. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3102-3116

[10] Discovery of Neuritogenic Compound Classes Inspired by Natural Products [J].

Dakas, Pierre-Yves ;

Parga, Juan A. ;

Hoeing, Susanne ;

Schoeler, Hans R. ;

Sterneckert, Jared ;

Kumar, Kamal ;

Waldmann, Herbert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (36) :9576-9581

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