Dimerization of Oxazolones by Copper-Catalyzed Cross-Dehydrogenative Coupling Reactions
Main Article Content
Abstract
A convenient and efficient cross-dehydrogenative coupling reaction by using readily available and inexpensive copper catalyst was reported. Several oxazolone derivatives underwent dimerization via the formation of Csp3-Csp3 bond under oxidative conditions in the presence of copper(II) acetate as a catalyst, di-tert-butyl peroxide as an oxidant, potassium carbonate as a base, and at high temperature. The dimerized products containing two quaternary centres were obtained in moderate to good yields, suggesting an approach to the synthesis of non-proteinogenic amino acids.
Keywords:
Oxazolone, azlactone, heterocycles, dimerization, copper catalysts, cross-dehydrogenative coupling.
References
[1] J. Venkatraman, S. C. Shankaramma, P. Balaram, Design of Folded Peptide, Chem. Rev, Vol. 101, 2001, pp. 3131.
[2] C. Toniolo, M. Crisna, F. Formaggio, C. Peggion, Control of Peptide Conformation by the Thorpe-Ingold Effect (C Alpha-tetrasubstitution), Biopolymers, Vol. 60, 2001, pp. 396.
[3] S. Gilead, E. Gazit, Inhibition of Amyloid Fibril Formation by Peptide Analogues Modified with α Aminoisobutyric Acid, Angew. Chem. Int. Ed., Vol. 43, 2004, pp. 4041.
[4] Y. Ohfune, T. Shinada, Synthesis of α,α-Diaryl-α-amino Acid Precursors by Reaction of Isocyanoacetate Esters with O-Quinone Diimides, Eur. J. Org. Chem, 2005, pp. 5127.
[5] D. Obrecht, M. Altorfer, C. Lehmann,
P. Schonholzer, K. Muller, General Synthesis of α-Acetoxy Ethers from Esters by DIBALH Reduction and Acetylation J. Org. Chem, Vol. 61, 1996, pp. 4080.
[6] J. S. Fisk, R. A. Mosey, J. J. Tepe, The Diverse Chemistry of Oxazol-5-(4H)-ones, Chem. Soc. Rev, Vol. 36, 2007, pp. 1432.
[7] M. Weber, W. Frey, R. Peters, Catalytic Asymmetric Synthesis of Functionalized
α,α-Disubstituted α-Amino Acid Derivatives from Racemic Unprotected α-Amino Acids via in-situ Generated Azlactones, Adv. Synth. Catal, Vol. 354, 2012, pp. 1443.
[8] N. Hewlett, C. Hupp, J. Tepe, Reactivity of Oxazol-5-(4H)-ones and Their Application toward Natural Product Synthesis, Synthesis, Vol. 17, 2009, pp. 2825-2839.
[9] J. M. Martínez, S. Reboredo, M. Izquierdo, V. Marcos, J. L. López, S. Filippone, N. Martín, Enantioselective Cycloaddition of Münchnones onto Fullerene: Organocatalysis Versus Metal Catalysis, J. Am. Chem. Soc, Vol. 136, 2014, pp. 2897.
[10] Z. Zhang, W. Sun, G. Zhu, J. Yang, M. Zhang, L. Hong, R. Wang, Chiral Phosphoric Acid Catalyzed Enantioselective 1,3-dipolar Cycloaddition Reaction of Azlactones, Chem. Commun, Vol. 52, 2016, pp. 1377.
[11] W. Sun, G. Zhu, C. Wu, G. Li, L. Hong, R. Wang, Organocatalytic Diastereo- and Enantioselective 1,3-dipolar Cycloaddition of Azlactones and Methyleneindolinones, Angew. Chem. Int. Ed, Vol. 52, 2013, pp. 8633.
[12] A. D. Melhado, M. Luparia, F. D. Toste, Au(I)-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions of Münchnones with Electron-Deficient Alkenes, J. Am. Chem. Soc, Vol. 129, 2007, pp. 12638.
[13] X. Chen, K. M. Engle, D. H. Wang, J. Q. Yi, Palladium(II)-Catalyzed C. H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality, Angew. Chem. Int. Ed., Vol. 48, No. 28, 2009, pp. 5049.
[14] C. J. Li, Cross-Dehydrogenative Coupling (CDC): Exploring C−C Bond Formations beyond Functional Group Transformations, Accounts of Chemical Research, Vol. 42, No. 2, 2009, pp. 335-344.
[2] C. Toniolo, M. Crisna, F. Formaggio, C. Peggion, Control of Peptide Conformation by the Thorpe-Ingold Effect (C Alpha-tetrasubstitution), Biopolymers, Vol. 60, 2001, pp. 396.
[3] S. Gilead, E. Gazit, Inhibition of Amyloid Fibril Formation by Peptide Analogues Modified with α Aminoisobutyric Acid, Angew. Chem. Int. Ed., Vol. 43, 2004, pp. 4041.
[4] Y. Ohfune, T. Shinada, Synthesis of α,α-Diaryl-α-amino Acid Precursors by Reaction of Isocyanoacetate Esters with O-Quinone Diimides, Eur. J. Org. Chem, 2005, pp. 5127.
[5] D. Obrecht, M. Altorfer, C. Lehmann,
P. Schonholzer, K. Muller, General Synthesis of α-Acetoxy Ethers from Esters by DIBALH Reduction and Acetylation J. Org. Chem, Vol. 61, 1996, pp. 4080.
[6] J. S. Fisk, R. A. Mosey, J. J. Tepe, The Diverse Chemistry of Oxazol-5-(4H)-ones, Chem. Soc. Rev, Vol. 36, 2007, pp. 1432.
[7] M. Weber, W. Frey, R. Peters, Catalytic Asymmetric Synthesis of Functionalized
α,α-Disubstituted α-Amino Acid Derivatives from Racemic Unprotected α-Amino Acids via in-situ Generated Azlactones, Adv. Synth. Catal, Vol. 354, 2012, pp. 1443.
[8] N. Hewlett, C. Hupp, J. Tepe, Reactivity of Oxazol-5-(4H)-ones and Their Application toward Natural Product Synthesis, Synthesis, Vol. 17, 2009, pp. 2825-2839.
[9] J. M. Martínez, S. Reboredo, M. Izquierdo, V. Marcos, J. L. López, S. Filippone, N. Martín, Enantioselective Cycloaddition of Münchnones onto Fullerene: Organocatalysis Versus Metal Catalysis, J. Am. Chem. Soc, Vol. 136, 2014, pp. 2897.
[10] Z. Zhang, W. Sun, G. Zhu, J. Yang, M. Zhang, L. Hong, R. Wang, Chiral Phosphoric Acid Catalyzed Enantioselective 1,3-dipolar Cycloaddition Reaction of Azlactones, Chem. Commun, Vol. 52, 2016, pp. 1377.
[11] W. Sun, G. Zhu, C. Wu, G. Li, L. Hong, R. Wang, Organocatalytic Diastereo- and Enantioselective 1,3-dipolar Cycloaddition of Azlactones and Methyleneindolinones, Angew. Chem. Int. Ed, Vol. 52, 2013, pp. 8633.
[12] A. D. Melhado, M. Luparia, F. D. Toste, Au(I)-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions of Münchnones with Electron-Deficient Alkenes, J. Am. Chem. Soc, Vol. 129, 2007, pp. 12638.
[13] X. Chen, K. M. Engle, D. H. Wang, J. Q. Yi, Palladium(II)-Catalyzed C. H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality, Angew. Chem. Int. Ed., Vol. 48, No. 28, 2009, pp. 5049.
[14] C. J. Li, Cross-Dehydrogenative Coupling (CDC): Exploring C−C Bond Formations beyond Functional Group Transformations, Accounts of Chemical Research, Vol. 42, No. 2, 2009, pp. 335-344.