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.
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收藏
页码：12354 / 12357
页数：4
相关论文
共 114 条
[1]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[2]   Organocatalysis - Organocatalysis lost: Modern chemistry, ancient chemistry, and an unseen biosynthetic apparatus [J].
Barbas, Carlos F., III .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) :42-47
[3]   Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters [J].
Bencivenni, Giorgio ;
Wu, Li-Yuan ;
Mazzanti, Andrea ;
Giannichi, Berardino ;
Pesciaioli, Fabio ;
Song, Mao-Ping ;
Bartoli, Giuseppe ;
Melchiorre, Paolo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (39) :7200-7203
[4]   Organocatalysis-after the gold rush [J].
Bertelsen, Soren ;
Jorgensen, Karl Anker .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189
[5]   CYCLOPIAMINES-A AND CYCLOPIAMINES-B NOVEL OXINDOLE METABOLITES OF PENICILLIUM-CYCLOPIUM WESTLING [J].
BOND, RF ;
BOEYENS, JCA ;
HOLZAPFEL, CW ;
STEYN, PS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (07) :1751-1761
[6]   A general synthetic entry to Strychnos alkaloids of the curan type via a common 3a-(2-nitrophenyl)hexahydroindol-4-one intermediate. Total syntheses of (+/-)- and (-)-tubifolidine, (+/-)-akuammicine, (+/-)-19,20-dihydroakuammicine, (+/-)-norfluorocurarine, (+/-)-echitamidine, and (+/-)-20-epilochneridine [J].
Bonjoch, J ;
Sole, D ;
GarciaRubio, S ;
Bosch, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (31) :7230-7240
[7]   Synthesis of strychnine [J].
Bonjoch, J ;
Solé, D .
CHEMICAL REVIEWS, 2000, 100 (09) :3455-3482
[8]   Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+)-Physostigmine [J].
Bui, Tommy ;
Syed, Salahuddin ;
Barbas, Carlos F., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :8758-+
[9]   An unexpected organocatalytic asymmetric tandem Michael/Morita-Baylis-Hillman reaction [J].
Cabrera, Silvia ;
Aleman, Jose ;
Bolze, Patrick ;
Bertelsen, Soren ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) :121-125
[10]   Urea and Thiourea-Functionalized Mesoporous Silica Nanoparticle Catalysts with Enhanced Catalytic Activity for Diels-Alder Reaction [J].
Chen, Hung-Ting ;
Trewyn, Brian G. ;
Wiench, Jerzy W. ;
Pruski, Marek ;
Lin, Victor S. -Y. .
TOPICS IN CATALYSIS, 2010, 53 (3-4) :187-191
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