Efficient selective formation of C-C single bonds and C=C double bonds by NBS-promoted oxidative coupling of β-keto esters

Synthetic Communications

Volumn 37, Issue 24, 2007, Pages 4399-4405

  Wang, Zhiguo ^a   Yin, Guodong ^a   Chen, Aihua ^a   Hu, Shengli ^a   Wu, Anxin ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

keto esters; Active methylene groups; NBS; Oxidative coupling

Indexed keywords

CARBENE; CARBON; ESTER DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; METHODOLOGY; OXIDATION;

EID: 37249091304     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701578123     Document Type: Article

References (24)

1. Linker, T.; Linker, U. Simple synthesis of tetra-Acceptor-substituted alkenes by the formal dehydrodimerization of malonates. Angew. Chem. Int. Ed. 2000, 39, 902.
2. Quast, H.; Seefelder, M.; Ivanova, S.; Heubes, M.; Peters, E. M.; Peters, K. Tetraacylethenes as dienophiles and hetero dienes in two-step Diels-Alder reactions. Eur. J. Org. Chem. 1999, 3343.
3. Wu, A.; Zhao, Y.; Chen, N.; Pan, X. A Modification of the knorr oxidative coupling method for preparation of 1,4-diketones. Synth. Commun. 1997, 27, 331.
4. Skarzewski, J.; Zon, J. Tetramethyl ethene-1,1,2,2-tetracarboxylate: oxidative homocoupling of dimethyl malonate in the presence of magnesium oxide. Synth. Commun. 1995, 25, 2953.
5. Liu, Y.-C.; Romero, J. R. Chemical and electrochemical oxidative dimerization of carbonyl compounds by cerium(IV) salts. a comparative Study. Tetrahedron Lett. 1995, 36, 8757.
6. Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Reactions of arylazosulfones with the conjugate bases of active-methylene compounds. Tetrahedron 1995, 51, 3905.
7. Villemin, D.; Alloum, A. B. Potassium fluoride on alumina: oxidative coupling of acidic carbon compounds with diiodine. Synth. Commun. 1992, 22, 3169.
8. Aidhen, I. S.; Narasimhan, N. S. Intramolecular arylation of soft carbon centre or enolate using Mn(III) acetate: studies towards spirostructure of fredericamycin A. Tetrahedron Lett. 1989, 30, 5323.
9. (a) Yang, D.; Yan, Y.-L.; Lui, B. Mild α-halogenation reactions of 1,3-dicarbonyl compounds catalyzed by lewis acids. J. Org. Chem. 2002, 67, 7429;
10. (b) Misra, A. P.; Raj, K.; Bhaduri, A. P. In Search of Imidazo [1,2-a] pyridine derivatives exhibiting resistance for catalytic hydrogenation. Synth. Commun. 1999, 29, 3227;
11. (c) Coats, S. J.; Wasserman, H. H. The conversion of α-bromob- dicarbonyls to vicinal tricarbonyls using dimethyldioxirane and base. Tetrahedron Lett. 1995, 36, 7735;
12. (d) Endo, M.; Droghini, R. 1-β-Methylcarbapenem intermediates Stereoselective synthesis of (3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-[(1R)-3-methoxycarbonyl-1-methyl-2- oxopropyl]azetidin-2-one and its related chemistry. Can. J. Chem. 1988, 66, 1400;
13. (e) Hlavka, J.; Bitha, P.; Lin, Y.; Strohmeyer, T. Reactions of 2,3-diamino-4(3H)-pyrimidinones. II. J. Heterocycl. Chem. 1985, 22, 1317;
14. (f) Yoshida, J.; Yano, S.; Ozawa, T.; Kawabata, N. Regioselective synthesis of dihydrofurans from 2,2-dibromo-1,3-diketone and olefin using copper. Tetrahedron Lett. 1984, 25, 2817;
15. (g) Kaye, P. T.; Meakins, G. D.; Smith, A. K.; Tirel, M. D. N,N-disubstituted 2-aminothiazole-5-carboxylates: preparation and rotation of functional groups. J. Chem. Soc., Perkin Trans. 1 1983, 1677.
16. (a) Boyd, R. E.; Rasmussen, C. R.; Press, J. B. Regiospecific synthesis of unsymmetrical α-bromoketones. Synth. Commun. 1995, 25, 1045;
17. (b) Karimi, S.; Grohmann, K. G. Intramolecular ring-opening of cyclopropanones by enolate anions. J. Org. Chem. 1995, 60, 554;
18. (c) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. Rate constants for halogen atom transfer from representative α-halo carbonyl compounds to primary alkyl radicals. J. Org. Chem. 1989, 54, 1826;
19. (d) Curran, D. P.; Chang, C. T. Atom transfer cyclization reactions of α-iodo esters, ketones, and malonates: examples of selective 5-exo, 6-endo, 6-exo, and 7-endo ring closures. J. Org. Chem. 1989, 54, 3140.
20. Wang, Z.; Chen, A.; Yin, G.; Wu, A. Diethyl 2,3-bis(benzo[1,3]dioxole-5- carbonyl)-but-2-enedioate. Acta Cryst. 2005, E61, o2320.
21. 1 I. Proton chemical shifts and equilibrium constants of pure compounds. J. Am. Chem. Soc. 1964, 86, 2105.
22. (a) Schaefer, J. P.; Wheatley, P. J. The crystal and molecular structure of tetra-acetylethane. J. Chem. Soc. A 1966, 528;
23. (b) Power, L. F.; Turner, K. E.; Moore, F. H. J. Refinement of the crystal and molecular structure of tetraacetylethane by neutron diffraction. Cryst. Mol. Struct. 1975, 5, 59;
24. (c) Lyssenko, K. A.; Lyubetsky, D. V.; Antipin, M. Y. Intramolecular H-bonds in the crystal of tetraacetylethane: 3c-4e interaction or a dynamic disorder?. Mendeleev Commun. 2003, 13, 60.