Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates

被引:140
作者
Han, Xiaoyu [1 ]
Chan, Wai-Lun [2 ]
Yao, Weijun [2 ]
Wang, Yongjiang [1 ]
Lu, Yixin [2 ]
机构
[1] Zhejiang Univ Sci & Technol, Zhejiang Prov Key Lab Chem & Biol Proc Technol Fa, Sch Biol & Chem Engn, Sch Light Ind, 318 Liuhe Rd, Hangzhou 310023, Zhejiang, Peoples R China
[2] Natl Univ Singapore NUS, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore
基金
中国国家自然科学基金;
关键词
3+2] cycloaddition; acyclic ketimines; amino acids; phosphine catalysts; spirooxindoles; BAYLIS-HILLMAN REACTION; ASYMMETRIC 3+2 CYCLOADDITION; VICINAL TETRASUBSTITUTED STEREOCENTERS; CATALYZED 4+2 ANNULATION; AZA-HENRY REACTION; MANNICH REACTION; ONE-POT; 1,3-DIPOLAR CYCLOADDITION; CHIRAL PHOSPHINES; GAMMA-ADDITION;
D O I
10.1002/anie.201600453
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Phosphine-catalyzed enantioselective annulation reactions involving ketimines are a daunting synthetic challenge owing to the intrinsic low reactivity of ketimine substrates. A highly enantioselective [3+2] cycloaddition reaction that makes use of isatin-derived ketimines as reaction partners was developed. Notably, both simple and gamma-substituted allenoates could be utilized, and various 3,2'-pyrrolidinyl spirooxindoles with a tetrasubstituted stereocenter were obtained in excellent yields and with nearly perfect enantioselectivity (>98% ee in all cases).
引用
收藏
页码:6492 / 6496
页数:5
相关论文
共 125 条
[1]   The ever-expanding role of asymmetric covalent organocatalysis in scalable, natural product synthesis [J].
Abbasov, Mikail E. ;
Romo, Daniel .
NATURAL PRODUCT REPORTS, 2014, 31 (10) :1318-1327
[2]   A Facile Ionic Liquid Promoted Synthesis, Cholinesterase Inhibitory Activity and Molecular Modeling Study of Novel Highly Functionalized Spiropyrrolidines [J].
Almansour, Abdulrahman I. ;
Kumar, Raju Suresh ;
Arumugam, Natarajan ;
Basiri, Alireza ;
Kia, Yalda ;
Ali, Mohamed Ashraf ;
Farooq, Mehvish ;
Murugaiyah, Vikneswaran .
MOLECULES, 2015, 20 (02) :2296-2309
[3]   A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides [J].
Almansour, Abdulrahman I. ;
Arumugam, Natarajan ;
Kumar, Raju Suresh ;
Periyasami, Govindasami ;
Ghabbour, Hazem A. ;
Fun, Hoong-Kun .
MOLECULES, 2015, 20 (01) :780-791
[4]   Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3+2] annulation [J].
Andrews, Ian P. ;
Kwon, Ohyun .
CHEMICAL SCIENCE, 2012, 3 (08) :2510-2514
[5]  
[Anonymous], ANGEW CHEM
[6]  
[Anonymous], 2015, ANGEW CHEM
[7]  
[Anonymous], 2015, ANGEW CHEM
[8]  
[Anonymous], 2013, ANGEW CHEM
[9]  
[Anonymous], ORG BIOMOL CHEM
[10]  
[Anonymous], 2015, Angew. Chem., Int. Ed.