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A Phosphine-Catalyzed [3 + 2] Annulation Reaction of Modified Allylic Compounds and N-Tosylimines
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Abstract
A phosphine-catalyzed annulation of modified allylic ylides with various aromatic imines to form 3-pyrrolines was developed. The presence of a substituent in the allylic compound is crucial for this reaction. Without the substituent, (E)-dienylimines will be produced via the dimerization of the allylic compounds.
Citing Articles
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This article has been cited by 15 ACS Journal articles (5 most recent appear below).
Divergent Amine-Catalyzed [4 + 2] Annulation of Morita–Baylis–Hillman Allylic Acetates with Electron-Deficient Alkenes
Silong Xu, Rongshun Chen, Zifeng Qin, Guiping Wu, and Zhengjie HeOrganic Letters2012 Article ASAPDivergent Amine-Catalyzed [4 + 2] Annulation of Morita–Baylis–Hillman Allylic Acetates with Electron-Deficient Alkenes
Silong Xu, Rongshun Chen, Zifeng Qin, Guiping Wu, and Zhengjie HeOrganic Letters2012 Article ASAPAn amine-catalyzed [4 + 2] annulation of Morita–Baylis–Hillman allylic acetates 2 with electron-deficient alkenes or diazenes has been developed for efficient syntheses of highly functionalized cyclohexenes, tetrahydropyridazines, and important ...
Tertiary Amine-Catalyzed Chemoselective and Asymmetric [3 + 2] Annulation of Morita–Baylis–Hillman Carbonates of Isatins with Propargyl Sulfones
Jing Peng, Xin Huang, Lin Jiang, Hai-Lei Cui, and Ying-Chun ChenOrganic Letters2011 Article ASAPTertiary Amine-Catalyzed Chemoselective and Asymmetric [3 + 2] Annulation of Morita–Baylis–Hillman Carbonates of Isatins with Propargyl Sulfones
Jing Peng, Xin Huang, Lin Jiang, Hai-Lei Cui, and Ying-Chun ChenOrganic Letters2011 Article ASAPA chemo- and enantioselective [3 + 2] annulation of Morita–Baylis–Hillman carbonates of isatins with propargyl sulfones was catalyzed by a β-ICD O-MOM ether 1c, affording spirocyclic 2-oxindoles bearing an unusual cyclopentadiene motif in outstanding ee ...
Highly Regio- and Diastereoselective Construction of Spirocyclopenteneoxindoles through Phosphine-Catalyzed [3 + 2] Annulation of Morita–Baylis–Hillman Carbonates with Isatylidene Malononitriles
Hong-Ping Deng, Yin Wei, and Min ShiOrganic Letters2011 Article ASAPHighly Regio- and Diastereoselective Construction of Spirocyclopenteneoxindoles through Phosphine-Catalyzed [3 + 2] Annulation of Morita–Baylis–Hillman Carbonates with Isatylidene Malononitriles
Hong-Ping Deng, Yin Wei, and Min ShiOrganic Letters2011 Article ASAPPhosphine-catalyzed highly regio- and diastereoselective [3 + 2] annulation of Morita–Baylis–Hillman (MBH) carbonates with isatylidene malononitriles has been disclosed to give the corresponding spirocyclopenteneoxindoles in excellent yields under mild ...
Core-Structure-Motivated Design of a Phosphine-Catalyzed [3 + 2] Cycloaddition Reaction: Enantioselective Syntheses of Spirocyclopenteneoxindoles
Bin Tan, Nuno R. Candeias, and Carlos F. Barbas, IIIJournal of the American Chemical Society2011 133 (13), 4672-4675Core-Structure-Motivated Design of a Phosphine-Catalyzed [3 + 2] Cycloaddition Reaction: Enantioselective Syntheses of Spirocyclopenteneoxindoles
Bin Tan, Nuno R. Candeias, and Carlos F. Barbas, IIIJournal of the American Chemical Society2011 133 (13), 4672-4675A novel organocatalytic asymmetric [3 + 2] cycloaddition reaction between methyleneindolinones and allylic compounds yielding complex spirocyclopentaneoxindoles has been developed. It provides extraordinary levels of enantioselective control involving a ...
Phosphine-Catalyzed [4 + 1] Annulation between α,β-Unsaturated Imines and Allylic Carbonates: Synthesis of 2-Pyrrolines
Junjun Tian, Rong Zhou, Haiyun Sun, Haibin Song, and Zhengjie HeThe Journal of Organic Chemistry2011 76 (7), 2374-2378Phosphine-Catalyzed [4 + 1] Annulation between α,β-Unsaturated Imines and Allylic Carbonates: Synthesis of 2-Pyrrolines
Junjun Tian, Rong Zhou, Haiyun Sun, Haibin Song, and Zhengjie HeThe Journal of Organic Chemistry2011 76 (7), 2374-2378In this report, a phosphine-catalyzed [4 + 1] annulation between α,β-unsaturated imines and allylic carbonates is described. This reaction represents the first realization of catalytic [4 + 1] cyclization of 1,3-azadienes with in situ formed phosphorus ...
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History
- Published In Issue October 16, 2008
- Article ASAPSeptember 11, 2008
- Received: July 23, 2008
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