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An Expedient Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Highly Functionalized Tetrahydropyridines
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Abstract
Ethyl 2-methyl-2,3-butadienoate acts as a 1,4-dipole synthon and undergoes [4 + 2] annulation with N-tosylimines in the presence of an organic phosphine catalyst. The resulting adducts, ethyl 6-substituted-1-(4-tosyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylates, are formed in excellent yields with complete regioselectivity. Mechanistic reasoning for this new annulation has led to an expansion of the reaction scope by employing ethyl 2-(substituted-methyl)-2,3-butadienoates to give ethyl 2,6-cis-disubstituted-1-(4-tosyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylates with high diastereoselectivities.
Citing Articles
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This article has been cited by 62 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 ...
Phosphine-Initiated General Base Catalysis: Facile Access to Benzannulated 1,3-Diheteroatom Five-Membered Rings via Double-Michael Reactions of Allenes
Judy Szeto, Vardhineedi Sriramurthy, and Ohyun KwonOrganic Letters2011 13 (20), 5420-5423Phosphine-Initiated General Base Catalysis: Facile Access to Benzannulated 1,3-Diheteroatom Five-Membered Rings via Double-Michael Reactions of Allenes
Judy Szeto, Vardhineedi Sriramurthy, and Ohyun KwonOrganic Letters2011 13 (20), 5420-5423General base-catalyzed double-Michael reactions of allenes with various dinucleophiles are described. The reactions are facilitated most efficiently by a catalytic amount of trimethylphosphine, affording six types of C2-functionalized benzannulated five-...
PPh2Me-Mediated Tandem Reaction of 2-Alkyl-2,3-butadienoates with Isothiocyanates: Formation of 2-Aminothiophenes
Xiao-Yang Guan and Min ShiACS Catalysis2011 1 (10), 1154-1157PPh2Me-Mediated Tandem Reaction of 2-Alkyl-2,3-butadienoates with Isothiocyanates: Formation of 2-Aminothiophenes
Xiao-Yang Guan and Min ShiACS Catalysis2011 1 (10), 1154-11572-Aminothiophenes were obtained through a PPh2Me-mediated tandem reaction of 2-alkyl-2,3-butadienoates with isothiocyanates, which involves an annulation of 2-alkyl-2,3-butadienoates with isothiocyanates and a subsequent umpolung addition to 2-alkyl-2,3-...
PBu3-Mediated Vinylogous Wittig Reaction of α-Methyl Allenoates with Aldehydes and Mechanistic Investigations
Silong Xu, Rongshun Chen, and Zhengjie HeThe Journal of Organic Chemistry2011 76 (18), 7528-7538PBu3-Mediated Vinylogous Wittig Reaction of α-Methyl Allenoates with Aldehydes and Mechanistic Investigations
Silong Xu, Rongshun Chen, and Zhengjie HeThe Journal of Organic Chemistry2011 76 (18), 7528-7538A highly stereoselective PBu3-mediated vinylogous Wittig olefination between α-methyl allenoates and a variety of aldehydes is presented as the first example of a practical and synthetically useful vinylogous Wittig reaction. Mechanistic experiments ...
Phosphine-Catalyzed Annulations of Azomethine Imines: Allene-Dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] Pathways
Risong Na, Chengfeng Jing, Qihai Xu, Hui Jiang, Xi Wu, Jiayan Shi, Jiangchun Zhong, Min Wang, Diego Benitez, Ekaterina Tkatchouk, William A. Goddard, III, Hongchao Guo, and Ohyun KwonJournal of the American Chemical Society2011 133 (34), 13337-13348Phosphine-Catalyzed Annulations of Azomethine Imines: Allene-Dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] Pathways
Risong Na, Chengfeng Jing, Qihai Xu, Hui Jiang, Xi Wu, Jiayan Shi, Jiangchun Zhong, Min Wang, Diego Benitez, Ekaterina Tkatchouk, William A. Goddard, III, Hongchao Guo, and Ohyun KwonJournal of the American Chemical Society2011 133 (34), 13337-13348In this paper we describe the phosphine-catalyzed [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] annulations of azomethine imines and allenoates. These processes mark the first use of azomethine imines in nucleophilic phosphine catalysis, producing dinitrogen-...
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History
- Published In Issue April 23, 2003
- Received January 29, 2003
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