Organocatalytic Asymmetric Formal [4+2] Cycloaddition for the Synthesis of Spiro[4-cyclohexanone-1,3′-oxindoline] Derivatives in High Optical Purity

被引:222
作者
Wei, Qiang
Gong, Liu-Zhu [1 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
关键词
X-RAY-ANALYSIS; ENANTIOSELECTIVE CONSTRUCTION; ALPHA; BETA-UNSATURATED IMIDES; MICHAEL ADDITION; CARBON CENTERS; ALKALOIDS; MARCFORTINE; ENANTIOMER; OXINDOLES; POTENT;
D O I
10.1021/ol100020v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A bifunctional organocatalytic asymmetric formal [4 + 2] cycloaddition reaction of Nazarov reagents and methyleneindolinones afforded spiro[4-cyclohexanone-1,3'-oxindoline] derivatives with excellent enantioselectivity (up to 98% ee).
引用
收藏
页码:1008 / 1011
页数:4
相关论文
共 37 条
[1]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[2]  
[Anonymous], 2008, CCDC 897144 (51) and CCDC 897143 (7) contain the Supplementary crystallographic data for this Letter, Patent No. [2008055812, 2008/055812]
[3]   Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].
Ashimori, A ;
Bachand, B ;
Overman, LE ;
Poon, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6477-6487
[4]   CATALYTIC ASYMMETRIC-SYNTHESIS OF QUARTERNARY CARBON CENTERS - PALLADIUM-CATALYZED FORMATION OF EITHER ENANTIOMER OF SPIROOXINDOLES AND RELATED SPIROCYCLICS USING A SINGLE ENANTIOMER OF A CHIRAL DIPHOSPHINE LIGAND [J].
ASHIMORI, A ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4571-4572
[5]   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
[6]   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-+
[7]   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
[8]  
*CCDC, 740395 CCDC
[9]   Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity [J].
Chen, Xiao-Hua ;
Wei, Qiang ;
Luo, Shi-Wei ;
Xiao, Han ;
Gong, Liu-Zhu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) :13819-13825
[10]   Catalytic asymmetric synthesis of all-carbon quaternary stereocenters [J].
Douglas, CJ ;
Overman, LE .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5363-5367