Efficient Selective Formation of C‐C Single Bonds and C˭C Double Bonds by NBS‐Promoted Oxidative Coupling of β‐Keto Esters

References

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