1,4-Conjugate addition/esterification of ortho-quinone methides in a multicomponent reaction

被引:32
作者
Chen, Renjie [1 ]
Liu, Yu [2 ]
Cui, Sunliang [1 ]
机构
[1] Zhejiang Univ, Coll Pharmaceut Sci, Inst Drug Discovery & Design, Hangzhou 310058, Zhejiang, Peoples R China
[2] Zhejiang Univ, Coll Life Sci, Sate Key Lab Plant Physiol & Biochem, Hangzhou 310058, Zhejiang, Peoples R China
关键词
ENANTIOSELECTIVE SYNTHESIS; YNAMIDES; CHEMISTRY; CYCLOADDITION; GENERATION; CATALYSIS; NITRILES; INDOLES; YLIDES; AZIDES;
D O I
10.1039/c8cc07328g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel 1,4-conjugate addition/esterification of ortho-quinone methides in a multicomponent reaction has been developed. In this protocol, numerous carboxylic acids, ynamides and in situ generated ortho-quinone methides could assemble rapidly to constitute this process for the synthesis of functionalized 3,3-diarylpropanamides with sufficient structural diversity. Furthermore, the products could be transformed to an array of compounds.
引用
收藏
页码:11753 / 11756
页数:4
相关论文
共 67 条
[51]  
2-7
[52]   Natural Product Synthesis Using Multicomponent Reaction Strategies [J].
Toure, Barry B. ;
Hall, Dennis G. .
CHEMICAL REVIEWS, 2009, 109 (09) :4439-4486
[53]   o-quinone methides:: intermediates underdeveloped and underutilized in organic synthesis [J].
Van de Water, RW ;
Pettus, TRR .
TETRAHEDRON, 2002, 58 (27) :5367-5405
[54]   Ynamides in Ring Forming Transformations [J].
Wang, Xiao-Na ;
Yeom, Hyun-Suk ;
Fang, Li-Chao ;
He, Shuzhong ;
Ma, Zhi-Xiong ;
Kedrowski, Brant L. ;
Hsung, Richard P. .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :560-578
[55]   Metal-Free [2+2+2] Cycloaddition of Ynamides and Nitriles: Mild and Regioselective Synthesis of Fully Substituted Pyridines [J].
Wang, Yong ;
Song, Li-Juan ;
Zhang, Xinhao ;
Sun, Jianwei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (33) :9704-9708
[56]   Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters [J].
Wang, Zhaobin ;
Wong, Yuk Fai ;
Sun, Jianwei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (46) :13711-13714
[57]   ortho-Quinone Methides in Natural Product Synthesis [J].
Willis, Nicky J. ;
Bray, Christopher D. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (30) :9160-9173
[58]   Development of a Convergent Entry to the Diazofluorene Antitumor Antibiotics: Enantioselective Synthesis of Kinamycin F [J].
Woo, Christina M. ;
Lu, Liang ;
Gholap, Shivajirao L. ;
Smith, Devin R. ;
Herzon, Seth B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (08) :2540-+
[59]   Metal-free hydroacyloxylation and hydration reactions of ynamides: synthesis of α-acyloxyenamides and N-acylsulfonamides [J].
Xu, Shijie ;
Liu, Jianquan ;
Hu, Donghua ;
Bi, Xihe .
GREEN CHEMISTRY, 2015, 17 (01) :184-187
[60]   Synthesis of Indoles through Highly Efficient Cascade Reactions of Sulfur Ylides and N-(ortho-Chloromethyl)aryl Amides [J].
Yang, Qing-Qing ;
Xiao, Cong ;
Lu, Liang-Qiu ;
An, Jing ;
Tan, Fen ;
Li, Bin-Jie ;
Xiao, Wen-Jing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) :9137-9140