An Organocatalytic Cascade Strategy for the Enantioselective Construction of Spirocyclopentane Bioxindoles Containing Three Contiguous Stereocenters and Two Spiro Quaternary Centers

被引:151
作者
Sun, Wangsheng [1 ]
Zhu, Gongming [1 ]
Wu, Chongyang [1 ]
Hong, Liang [1 ]
Wang, Rui [1 ]
机构
[1] Lanzhou Univ, Inst Biochem & Mol Biol, Sch Basic Med Sci, Key Lab Preclin Study New Drugs Gansu Prov,Sch Li, Lanzhou 730000, Peoples R China
关键词
cascade reactions; methyleneindolinone; organocatalysis; spiro compounds; squaramides; CATALYTIC ASYMMETRIC-SYNTHESIS; MICHAEL-ALKYLATION REACTIONS; STRUCTURE-BASED DESIGN; ONE-POT SYNTHESIS; SPIROCYCLIC OXINDOLES; DIELS-ALDER; MULTIPLE STEREOCENTERS; CHIRAL SQUARAMIDES; NATURAL-PRODUCTS; DOMINO REACTIONS;
D O I
10.1002/chem.201200478
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A rapid and efficient organocatalytic cascade sequence for the direct construction of spirocyclopentane bioxindoles has been carried out by using a chiral squaramide catalyst in the presence of a base. This process constitutes a powerful approach to the preparation of biologically important bispirooxindoles in high enantioselectivities (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:6737 / 6741
页数:5
相关论文
共 87 条
[71]   Isolation of Antipodal (-)-Versicolamide B and Notoamides L-N from a Marine-Derived Aspergillus sp. [J].
Tsukamoto, Sachiko ;
Kawabata, Tetsuro ;
Kato, Hikaru ;
Greshock, Thomas J. ;
Hirota, Hiroshi ;
Ohta, Tornihisa ;
Williams, Robert M. .
ORGANIC LETTERS, 2009, 11 (06) :1297-1300
[72]   Catalytic asymmetric intramolecular α-alkylation of aldehydes [J].
Vignola, N ;
List, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :450-451
[73]   An Organocatalytic [3+2] Cyclisation Strategy for the Highly Enantioselective Synthesis of Spirooxindoles [J].
Voituriez, Arnaud ;
Pinto, Nathalie ;
Neel, Mathilde ;
Retailleau, Pascal ;
Marinetti, Angela .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (42) :12541-12544
[74]   A highly organocatalytic stereoselective double Michael reaction: efficient construction of optically enriched spirocyclic oxindoles [J].
Wang, Liang-Liang ;
Peng, Lin ;
Bai, Jian-Fei ;
Jia, Li-Na ;
Luo, Xi-Ya ;
Huang, Qing-Chun ;
Xu, Xiao-Ying ;
Wang, Li-Xin .
CHEMICAL COMMUNICATIONS, 2011, 47 (19) :5593-5595
[75]   Organocatalytic Asymmetric Formal [4+2] Cycloaddition for the Synthesis of Spiro[4-cyclohexanone-1,3′-oxindoline] Derivatives in High Optical Purity [J].
Wei, Qiang ;
Gong, Liu-Zhu .
ORGANIC LETTERS, 2010, 12 (05) :1008-1011
[76]   Paraherquamides, brevianamides, and asperparalines: Laboratory synthesis and biosynthesis. An interim report [J].
Williams, RM ;
Cox, RJ .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (02) :127-139
[77]   Organocatalytic enantioselective cascade Michael-alkylation reactions: Synthesis of chiral cyclopropanes and investigation of unexpected organocatalyzed stereoselective ring opening of cyclopropanes [J].
Xie, Hexin ;
Zu, Liansuo ;
Li, Hao ;
Wang, Jian ;
Wang, Wei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (35) :10886-10894
[78]  
Xu B., 2012, ANGEW CHEM, V124, P1083
[79]   Multistep One-Pot Synthesis of Enantioenriched Polysubstituted Cyclopenta[b]indoles [J].
Xu, Biao ;
Guo, Zhi-Lei ;
Jin, Wan-Yan ;
Wang, Zhi-Ping ;
Peng, Yun-Gui ;
Guo, Qi-Xiang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) :1059-1062
[80]   Chiral Squaramides as Highly Enantioselective Catalysts for Michael Addition Reactions of 4-Hydroxycoumarins and 4-Hydroxypyrone to β,γ-Unsaturated α-Keto Esters [J].
Xu, Dan-Qian ;
Wang, Yi-Feng ;
Zhang, Wei ;
Luo, Shu-Ping ;
Zhong, Ai-Guo ;
Xia, Ai-Bao ;
Xu, Zhen-Yuan .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (14) :4177-4180