Highly Efficient Hydrogen-Bonding Catalysis of the Diels-Alder Reaction of 3-Vinylindoles and Methyleneindolinones Provides Carbazolespirooxindole Skeletons

被引：339
作者：
Tan, Bin [1 ,2 ,3 ]
Hernandez-Torres, Gloria [1 ,2 ,3 ,4 ]
Barbas, Carlos F., III [1 ,2 ,3 ]
机构：
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[3] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
[4] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 32期
关键词：
ALPHA; BETA-UNSATURATED KETONES; ENANTIOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC ORGANOCATALYSIS; STEREOSELECTIVE-SYNTHESIS; SPIROCYCLIC OXINDOLES; NONCOVALENT CATALYSIS; CONJUGATE ADDITION; DOMINO REACTIONS; MICHAEL REACTION;
D O I：
10.1021/ja203812h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Carbazolespirooxindole derivatives were synthesized in a high-yielding, atypically rapid, stereocontrolled Diels-Alder reaction catalyzed by a C-2-symmetric bisthiourea organocatalyst. Simple precursors and mild conditions were used to construct carbazolespirooxindole derivatives with high enantiopurity and structural diversity under H-bonding catalysis. The practical approach recycles the organocatalyst and solvent. This simple and efficient operational procedure will allow diversity-oriented syntheses of this intriguing class of compounds.
引用
收藏
页码：12354 / 12357
页数：4
相关论文
共 114 条
[21]   Density functional study of noncovalent catalysis of the Diels-Alder reaction by the neutral hydrogen bond donors thiourea and urea [J].
Fu, Aiping ;
Thiel, Walter .
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2006, 765 (1-3) :45-52
[22]   Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents [J].
Galliford, Chris V. ;
Scheidt, Karl A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8748-8758
[23]   Enantioselective organocatalysis [J].
Gaunt, Matthew J. ;
Johansson, Carin C. C. ;
McNally, Andy ;
Vo, Ngoc T. .
DRUG DISCOVERY TODAY, 2007, 12 (1-2) :8-27
[24]   Organocatalytic Asymmetric Diels-Alder Reactions of 3-Vinylindoles [J].
Gioia, Claudio ;
Hauville, Agnes ;
Bernardi, Luca ;
Fini, Francesco ;
Ricci, Alfredo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (48) :9236-9239
[25]   Hydrogen bonding catalysis operates by charge stabilization in highly polar diels-alder reactions [J].
Gordillo, Ruth ;
Dudding, Travis ;
Anderson, Christopher D. ;
Houk, K. N. .
ORGANIC LETTERS, 2007, 9 (03) :501-503
[26]   VINCA ALKALOIDS .10. STRUCTURE OF VINDOLINE [J].
GORMAN, M ;
NEUSS, N ;
BIEMANN, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (06) :1058-&
[27]   Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600 [J].
Greshock, Thomas J. ;
Grubbs, Alan W. ;
Jiao, Ping ;
Wicklow, Donald T. ;
Gloer, James B. ;
Williams, Robert M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (19) :3573-3577
[28]   Organocatalytic Regio- and Stereoselective Inverse-Electron-Demand Aza-Diels-Alder Reaction of α,β-Unsaturated Aldehydes and N-Tosyl-1-aza-1,3-butadienes [J].
Han, Bo ;
He, Zhao-Quan ;
Li, Jun-Long ;
Li, Rui ;
Jiang, Kun ;
Liu, Tian-Yu ;
Chen, Ying-Chun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (30) :5474-5477
[29]   Organocatalytic Asymmetric Inverse-Electron-Demand Aza-Diels-Alder Reaction of N-Sulfonyl-1-aza-1,3-butadienes and Aldehydes [J].
Han, Bo ;
Li, Jun-Long ;
Ma, Chao ;
Zhang, Shan-Jun ;
Chen, Ying-Chun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (51) :9971-9974
[30]   Asymmetric Diels-Alder reactions of α,β-unsaturated aldehydes catalyzed by a diarylprolinol silyl ether salt in the presence of water [J].
Hayashi, Yujiro ;
Samanta, Sampak ;
Gotoh, Hiroaki ;
Ishikawa, Hayato .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (35) :6634-6637
12345678910