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
收藏
页码：4126 / 4129
页数：4
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共 89 条
[21]   Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates [J].
Han, Xiaoyu ;
Chan, Wai-Lun ;
Yao, Weijun ;
Wang, Yongjiang ;
Lu, Yixin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (22) :6492-6496
[22]   Asymmetric Synthesis of Spiropyrazolones through Phosphine-Catalyzed [4+1] Annulation [J].
Han, Xiaoyu ;
Yao, Weijun ;
Wang, Tianli ;
Tan, Yong Ren ;
Yan, Ziyu ;
Kwiatkowski, Jacek ;
Lu, Yixin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) :5643-5647
[23]   Versatile Enantioselective [3+2] Cyclization between Imines and Allenoates Catalyzed by Dipeptide-Based Phosphines [J].
Han, Xiaoyu ;
Zhong, Fangrui ;
Wang, Youqing ;
Lu, Yixin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (03) :767-770
[24]   Formation of Functionalized Cyclopentenes via Catalytic Asymmetric [3+2] Cycloaddition of Acrylamides with an Allenoate Promoted by Dipeptide-Derived Phosphines [J].
Han, Xiaoyu ;
Wang, Su-Xi ;
Zhong, Fangrui ;
Lu, Yixin .
SYNTHESIS-STUTTGART, 2011, (12) :1859-1864
[25]   Enantioselective [3+2] Cycloaddition of Allenes to Acrylates Catalyzed by Dipeptide-Derived Phosphines: Facile Creation of Functionalized Cyclopentenes Containing Quaternary Stereogenic Centers [J].
Han, Xiaoyu ;
Wang, Youqing ;
Zhong, Fangrui ;
Lu, Yixin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (06) :1726-1729
[26]   Ortho-Quinone Methides as Reactive Intermediates in Asymmetric Bronsted Acid Catalyzed Cycloadditions with Unactivated Alkenes by Exclusive Activation of the Electrophile [J].
Hsiao, Chien-Chi ;
Raja, Sadiya ;
Liao, Hsuan-Hung ;
Atodiresei, Iuliana ;
Rueping, Magnus .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) :5762-5765
[27]   Enantio- and Diastereoselective Access to Distant Stereocenters Embedded within Tetrahydroxanthenes: Utilizing ortho-Quinone Methides as Reactive Intermediates in Asymmetric Bronsted Acid Catalysis [J].
Hsiao, Chien-Chi ;
Liao, Hsuan-Hung ;
Rueping, Magnus .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (48) :13258-13263
[28]   Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(III)-complex catalyzed inverse-electron-demand hetero-Diels-Alder reaction [J].
Hu, Haipeng ;
Liu, Yangbin ;
Guo, Jing ;
Lin, Lili ;
Xu, Yali ;
Liu, Xiaohua ;
Feng, Xiaoming .
CHEMICAL COMMUNICATIONS, 2015, 51 (18) :3835-3837
[29]   Asymmetric Total Synthesis of the Iridoid β-Glucoside (+)-Geniposide via Phosphine Organocatalysis [J].
Jones, Regan A. ;
Krische, Michael J. .
ORGANIC LETTERS, 2009, 11 (08) :1849-1851
[30]   Enantioselective Rauhut-Currier-Type 1,6-Conjugate Addition of Methyl Vinyl Ketone to para-Quinone Methides [J].
Kang, Tian-Chen ;
Wu, Lu-Ping ;
Yu, Qi-Wen ;
Wu, Xin-Yan .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (27) :6509-6513
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