DFT study on the mechanisms and diastereoselectivities of Lewis acid-promoted ketene-alkene [2 + 2] cycloadditions: What is the role of Lewis acid in the ketene and C = X (X = O, CH2, and NH) [2 + 2] cycloaddition reactions?

Journal of Physical Chemistry A

Volumn 118, Issue 24, 2014, Pages 4288-4300

  Wang, Yang ^a   Wei, Donghui ^a   Li, Zhenyu ^a   Zhu, Yanyan ^a   Tang, Mingsheng ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ENERGY BARRIERS; HYDROCARBONS; KETONES; MOLECULAR ORBITALS; STEREOSELECTIVITY;

COMPUTATIONAL RESULTS; DIASTEREOSELECTIVITIES; FRONTIER MOLECULAR ORBITALS; INTERACTION MODES; INTRINSIC REACTION COORDINATE; REACTIVITY INDICES;

CYCLOADDITION;

EID: 84902960266     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp500358m     Document Type: Article

References (85)

1. Staudinger, H. Ketene, Eine Neue Körperklasse Chem. Ber. 1905, 38, 1735-1739
2. Staudinger, H. Über Ketene. 4. Mitteilung: Reaktionen des Diphenylketens Chem. Ber. 1907, 40, 1145-1148
3. Snider, B. B. Intramolecular Cycloaddition Reactions of Ketenes and Keteniminium Salts with Alkenes Chem. Rev. 1988, 88, 793-811
4. Tidwell, T. T. Ketene Chemistry: The Second Golden Age Acc. Chem. Res. 1990, 23, 273-279
5. Tidwell, T. T. Blue, But not a Mirage: Stable Aminoketenes by Carbene Carbonylation Angew. Chem., Int. Ed. 2006, 45, 5580-5582
6. Tidwell, T. T. Ketene Chemistry After 100 Years: Ready for a New Century Eur. J. Org. Chem. 2006, 2006, 563-576
7. Liang, Y.; Jiao, L.; Zhang, S. W.; Xu, J. X. Microwave- and Photoirradiation-Induced Staudinger Reactions of Cyclic Imines and Ketenes Generated from α-Diazoketones. A Further Investigation into the Stereochemical Process J. Org. Chem. 2005, 70, 334-337
8. France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Advances in the Catalytic, Asymmetric Synthesis of β-Lactams Acc. Chem. Res. 2004, 37, 592-600
9. Reddy, L. R.; Corey, E. J. Novel Bicyclization Reaction Leading to a Fused β-Lactone Org. Lett. 2006, 8, 1717-1719
10. McCaleb, K. L.; Halcomb, R. L. Intramolecular Ketene-Allene Cycloadditions Org. Lett. 2000, 2, 2631-2634
11. Tidwell, T. T. Ketenes; Wiley: New York, 1995.
12. Tidwell, T. T. Ketenes II; Wiley: New York, 2006.
13. Lee, S. Y.; Kulkarni, Y. S.; Burbaum, B. W.; Johnston, M. I.; Sinder, B. B. Type I Intramolecular Cycloadditions of Vinylketenes J. Org. Chem. 1988, 53, 1848-1855
14. Evans, D. A.; Janey, J. M. C-2-Symmetric Cu(II) Complexes as Chiral Lewis Acids. Catalytic, Enantioselective Cycloadditions of Silyl Ketenes Org. Lett. 2001, 3, 2125-2128
15. 2-Mediated Tandem Mukaiyama Aldol Lactonization: Evidence for Asynchronous, Concerted Transition States and Discovery of 2-Oxopyridyl Ketene Acetal Variants J. Am. Chem. Soc. 2012, 134, 3084-3094
16. Rasik, C. M.; Brown, M. K. Lewis Acid-Promoted ketene-alkene [2 + 2] Cycloadditions J. Am. Chem. Soc. 2013, 135, 1673-1676
17. Cheong, P. H. Y.; Legault, C. Y.; Um, J. M.; Celebi-Olcum, N.; Houk, K. N. Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities Chem. Rev. 2011, 111, 5042-5137
18. Douglas, J.; Taylor, J. E.; Churchill, G.; Slawin, A. M. Z.; Smith, A. D. NHC-Promoted Asymmetric β-Lactone Formation from Arylalkylketenes and Electron-Deficient Benzaldehydes or Pyridinecarboxaldehydes J. Org. Chem. 2013, 78, 3925-3938
19. Wang, Y. K.; Liang, Y.; Jiao, L.; Du, D. M.; Xu, J. X. Do Reaction Conditions Affect the Stereoselectivity in the Staudinger Reaction? J. Org. Chem. 2006, 71, 6983-6990
20. Wei, D. H.; Wang, L. G.; Tang, M. S. A DFT Study on the Thermal Reaction Mechanisms of Fluorobutanesulfonyl Azide with Pyrazine under Solvent Free Condition Comput. Theor. Chem. 2011, 968, 39-43
21. Wang, X. N.; Zhang, Y. Y.; Ye, S. Enantioselective Synthesis of Spirocyclic Oxindole-β-Lactones via N-Heterocyclic Carbene-Catalyzed Cycloaddition of Ketenes and Isatins Adv. Synth. Catal. 2010, 352, 1892-1895
22. Wang, X. N.; Shao, P. L.; Lv, H.; Ye, S. Enantioselective Synthesis of β-Trifluoromethyl-β-Lactones via NHC-Catalyzed ketene-ketone Cycloaddition Reactions Org. Lett. 2009, 11, 4029-4031
23. Pons, J. M.; Pommier, A.; Rajzmann, M.; Liotard, D. Exploratory Theoretical-Study of the [2 + 2] Cycloaddition between Ketene and Formaldehyde J. Mol. Struct.: THEOCHEM 1994, 119, 361-364
24. Truong, T. N. Solvent Effects on Structure and Reaction Mechanism: A Theoretical Study of [2 + 2] Polar Cycloaddition between Ketene and Imine J. Phys. Chem. B 1998, 102, 7877-7881
25. Li, X. Y.; Xu, J. X. Annuloselectivity in Cycloadditions of Ketenes with Imines: A DFT Study J. Org. Chem. 2013, 78, 347-355
26. Wang, X. B.; Houk, K. N. Carbenoid Character in Transition Structures for Reactions of Ketenes with Alkenes J. Am. Chem. Soc. 1990, 112, 1754-1756
27. Kamiya, K.; Matsui, T.; Sugimura, T.; Shigeta, Y. Theoretical Insight into Stereoselective Reaction Mechanisms of 2,4-Pentanediol-Tethered Ketene-Olefin [2 + 2] Cycloaddition J. Phys. Chem. A 2012, 116, 1168-1175
28. Burke, L. A. Theoretical Study of [2 + 2] Cycloadditions. Kentene with Ethylene J. Org. Chem. 1985, 50, 3149-3155
29. Valenti, E.; Pericas, M. A.; Moyano, A. A Theoretical-Study on Ketene-Olefin Cycloadditions 0.1. Intermolecular Reactions J. Org. Chem. 1990, 55, 3582-3593
30. Cossio, F. P.; Ugalde, J. M.; Lopez, X.; Lecea, B.; Palomo, C. A Semiempirical Theoretical-Study on the Formation of β-Lactams from Ketenes and Imines J. Am. Chem. Soc. 1993, 115, 995-1004
31. Lecea, B.; Arrieta, A.; Arrastia, I.; Cossio, F. P. Origins of Stereocontrol in the [2 + 2] Cycloaddition between Achiral Ketenes and Chiral α-Alkoxy Aldehydes. A Pericyclic Alternative to the Aldol Reaction J. Org. Chem. 1998, 63, 5216-5227
32. Arrieta, A.; Lecea, B.; Cossio, F. P. Origins of the Stereodivergent Outcome in the Staudinger Reaction between Acyl Chlorides and Imines J. Org. Chem. 1998, 63, 5869-5876
33. Palomo, C.; Ganboa, I.; Kot, A.; Dembkowski, L. Practical Access to Carbacephem Intermediates via Asymmetric [2 + 2] Ketene-Imine Cycloaddition J. Org. Chem. 1998, 63, 6398-6400
34. Alajarin, M.; Vidal, A.; Tovar, F.; Arrieta, A.; Lecea, B.; Cossio, F. P. Surpassing Torquoelectronic Effects in Conrotatory Ring Closures: Origins of Stereocontrol in Intramolecular Ketenimine-Imine [2 + 2] Cycloadditions Chem.-Eur. J. 1999, 5, 1106-1117
35. Machiguchi, T.; Hasegawa, T.; Ishiwata, A.; Terashima, S.; Yamabe, S.; Minato, T. Ketene Recognizes 1,3-Dienes in their s-cis Forms through [4 + 2] (Diels-Alder) and [2 + 2] (Staudinger) Reactions. An Innovation of Ketene Chemistry J. Am. Chem. Soc. 1999, 121, 4771-4786
36. Arrieta, A.; Cossio, F. P.; Lecea, B. New Insights on the Origins of the Stereocontrol of the Staudinger Reaction: [2 + 2] Cycloaddition between Ketenes and N-silylimines J. Org. Chem. 2000, 65, 8458-8464
37. Venturini, A.; Gonzalez, J. A CASPT2 and CASSCF Approach to the Cycloaddition of Ketene and Imine: A New Mechanistic Scheme of the Staudinger Reaction J. Org. Chem. 2002, 67, 9089-9092
38. Machiguchi, T.; Okamoto, J.; Takachi, J.; Hasegawa, T.; Yamabe, S.; Minato, T. Exclusive Formation of α-Methyleneoxetanes in ketene-alkene Cycloadditions. Evidence for Intervention of both an α-Methyleneoxetane and the Subsequent 1,4-Zwitterion J. Am. Chem. Soc. 2003, 125, 14446-14448
39. Ramirez-Galicia, G.; Rubio, M. F.; Jimenez-Cruz, F. Intramolecular Competition between Alkenes in ketene-alkene [2 + 2] Cycloaddition. A Theoretical Study J. Mol. Struct.: THEOCHEM 2006, 773, 53-58
40. Cossio, F. P.; Arrieta, A.; Sierra, M. A. The Mechanism of the Ketene-Imine (Staudinger) Reaction in its Centennial: Still an Unsolved Problem? Acc. Chem. Res. 2008, 41, 925-936
41. Lecea, B.; Arrieta, A.; Lopez, X.; Ugalde, J. M.; Cossio, F. P. On the Stereochemical Outcome of the Catalyzed and Uncatalyzed Cycloaddition Reaction between Activated Ketenes and Aldehydes to Form cis-2-Oxetanones and trans-2-Oxetanones-an Ab-Initio Study J. Am. Chem. Soc. 1995, 117, 12314-12321
42. Lecea, B.; Arrieta, A.; Roa, G.; Ugalde, J. M.; Cossio, F. P. Catalytic and Solvent Effects on the Cycloaddition Reaction between Ketenes and Carbonyl-Compounds to Form 2-Oxetanones J. Am. Chem. Soc. 1994, 116, 9613-9619
43. Pons, J. M.; Oblin, M.; Pommier, A.; Rajzmann, M.; Liotard, D. Formation of β-Lactones through Lewis Acid-Promoted [2 + 2] Cycloaddition Reaction. A Theoretical Study J. Am. Chem. Soc. 1997, 119, 3333-3338
44. Yamabe, S.; Minato, T.; Osamura, Y. Dual One-centre Frontier-orbital Interactions in [2 + 2] Cycloadditions of Ketenes J. Chem. Soc., Chem. Commun. 1993, 5, 450-452
45. Yamabe, S.; Kuwata, K.; Minato, T. Frontier-orbital Analyses of Ketene [2 + 2] Cycloadditions Theor. Chem. Acc. 1999, 102, 139-146
46. 3? J. Mol. Catal. A: Chem. 2010, 326, 41-47
47. Asatryan, R.; Ruckenstein, E. Mechanism of Iron Carbonyl-catalyzed Hydrogenation of Ethylene.1. Theoretical Exploration of Molecular Pathways J. Phys. Chem. A 2013, 117, 10912-10932
48. Zhang, W. J.; Zhu, Y. Y.; Wei, D. H.; Tang, M. S. Mechanisms of the Cascade Synthesis of Substituted 4-amino-1,2,4-triazol-3-one from Huisgen Zwitterion and Aldehyde Hydrazone: A DFT Study J. Comput. Chem. 2012, 33, 715-722
49. Qiao, Y.; Han, K. L. Elucidation of the Reaction Mechanisms and Diastereoselectivities of Phosphine-Catalyzed [4 + 2] Annulations between Allenoates and Ketones or Aldimines Org. Biomol. Chem. 2012, 10, 7689-7706
50. Zhang, W. J.; Zhu, Y. Y.; Wei, D. H.; Li, Y. X.; Tang, M. S. Theoretical Investigations toward the [4 + 2] Cycloaddition of Ketenes with N-Benzoyldiazenes Catalyzed by N-Heterocyclic Carbenes: Mechanism and Enantioselectivity J. Org. Chem. 2012, 77, 10729-10737
51. Chen, H.; Wang, Z. F.; Zhang, Y. N.; Huang, Y. Highly trans-Stereoselective Synthesis of Bicyclic Isoxazolidines via Copper-Catalyzed Triple Cascade Catalysis J. Org. Chem. 2013, 78, 3503-3509
52. 2? Effect of a Shallow Intermediate in Gas-Phase Direct Dynamics Simulations J. Phys. Chem. A 2012, 116, 11492-11499
53. Bernstein, E. R.; Yu, Z. J. On the Decomposition Mechanisms of New Imidazole-Based Energetic Materials J. Phys. Chem. A 2013, 117, 1756-1764
54. Wei, D. H.; Lei, B. L.; Tang, M. S.; Zhan, C. G. Fundamental Reaction Pathway and Free Energy Profile for Inhibition of Proteasome by Epoxomicin J. Am. Chem. Soc. 2012, 134, 10436-10450
55. Wei, D. H.; Fang, L.; Tang, M. S.; Zhan, C. G. Fundamental Reaction Pathway for Peptide Metabolism by Proteasome J. Phys. Chem. B 2013, 117, 13418-13434
56. Wei, D. H.; Huang, X. Q.; Liu, J. J.; Tang, M. S.; Zhan, C. G. Reaction Pathway and Free Energy Profile for Papain-Catalyzed Hydrolysis of N-acetyl-Phe-Gly 4-Nitroanilide Biochemistry 2013, 52, 5145-5154
57. Zhang, W. J.; Truhlar, D. G.; Tang, M. S. Tests of Exchange-Correlation Functional Approximations Against Reliable Experimental Data for Average Bond Energies of 3d Transition Metal Compounds J. Chem. Theory Comput. 2013, 9, 3965-3977
58. 3X (X = Cl, Br, I): Exploring the Influence of Dipole Orientation on Association and C-X Bond Activation J. Phys. Chem. A 2012, 116, 3979-3988
59. Liu, Z.; Cheng, R. H.; He, X. L.; Wu, X. J.; Liu, B. P. DFT Functional Benchmarking on the Energy Splitting of Chromium Spin States and Mechanistic Study of Acetylene Cyclotrimerization over the Phillips Cr(II)/Silica Catalyst J. Phys. Chem. A 2012, 116, 7538-7549
60. 2-Fixation Intermediates J. Phys. Chem. A 2012, 116, 11618-11642
61. Liu, S.; Srinivasan, S.; Grady, M. C.; Soroush, M.; Rappe, A. M. Computational Study of Cyclohexanone-Monomer Co-initiation Mechanism in Thermal Homo-polymerization of Methyl Acrylate and Methyl Methacrylate J. Phys, Chem. A 2012, 116, 5337-5348
62. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A. Gaussian 09, revision C.01; Gaussian, Inc.: Wallingford, CT, 2010.
63. Becke, A. D. Density-Functional Thermochemistry 0.3. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
64. Lee, C. T.; Yang, W. T.; Parr, R. G. Development of the Colle-salvetti Correlation-Energy Formula into a Functional of the Electron-Density Phys. Rev. B 1988, 37, 785-789
65. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Results Obtained with the Correlation-Energy Density Functionals of Becke and Lee, Yang and Parr Chem. Phys. Lett. 1989, 157, 200-206
66. Barone, V.; Cossi, M. Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model J. Phys. Chem. A 1998, 102, 1995-2001
67. Mennucci, B.; Tomasi, J. Continuum Solvation Models: A New Approach to the Problem of Solute's Charge Distribution and Cavity Boundaries J. Chem. Phys. 1997, 106, 5151-5158
68. Gonzalez, C.; Schlegel, H. B. Reaction-Path Following in Mass-Weighted Internal Coordinates J. Phys. Chem. 1990, 94, 5523-5527
69. Gonzalez, C.; Schlegel, H. B. An Improved Algorithm for Reaction-Path Following J. Chem. Phys. 1989, 90, 2154-2161
70. Wei, D. H.; Zhu, Y. Y.; Zhang, C.; Sun, D. Z.; Zhang, W. J.; Tang, M. S. A DFT Study on Enantioselective Synthesis of Aza-β-Lactams via NHC-catalyzed [2 + 2] Cycloaddition of Ketenes with Diazenedicarboxylates J. Mol. Catal. A: Chem. 2011, 334, 108-115
71. nCr (n = 1-13) Clusters J. Phys. Chem. A 2013, 117, 3458-3466
72. Vektariene, A. Insights into the Mechanism of the Benzoannelated Thieno[3,2-b]Furan Halogenation. Importance of HOMO-HOMO Interaction J. Phys. Chem. A 2013, 117, 8449-8458
73. Pfaendtner, J.; Fleming, K. L. Characterizing the Catalyzed Hydrolysis of β-1,4-Glycosidic Bonds Using Density Functional Theory J. Phys. Chem. A 2013, 117, 14200-14208
74. Yamabe, S.; Dai, T.; Minato, T.; Machiguchi, T.; Hasegawa, T. Ketene Is a Dienophile for [4 + 2] (Diels-Alder) Reaction across Its C=O Bond J. Am. Chem. Soc. 1996, 118, 6518-6519
75. Fang, D. C.; Fu, X. Y. Ab Initio Study on the Mechanism of Cycloaddition Reaction of Ketene with Methylenimine: A New Reaction Scheme Int. J. Quantum Chem. 1992, 43, 669-676
76. Parr, R. G.; Pearson, R. G. Absolute Hardness Companion Parameter to Absolute Electronegativity J. Am. Chem. Soc. 1983, 105, 7512-7516
77. Domingo, L. R.; Saez, J. A.; Zaragoza, R. J.; Arno, M. Understanding the Participation of Quadricyclane as Nucleophile in Polar [2σ+2σ+2π] Cycloadditions toward Electrophilic π Molecules J. Org. Chem. 2008, 73, 8791-8799
78. Domingo, L. R.; Picher, M. T.; Saez, J. A. Toward an Understanding of the Unexpected Regioselective Hetero-Diels-Alder Reactions of Asymmetric Tetrazines with Electron-rich Ethylenes: A DFT Study J. Org. Chem. 2009, 74, 2726-2735
79. Domingo, L. R.; Aurell, M. J.; Perez, P.; Contreras, R. Quantitative Characterization of the Global Electrophilicity Power of Common Diene/Dienophile Pairs in Diels-Alder Reactions Tetrahedron 2002, 58, 4417-4423
80. Kohn, W.; Sham, L. J. Quantum Density Oscillations in an Inhomogeneous Electron Gas Phys. Rev. 1965, 137, 1697-1705
81. Sham, L. J.; Kohn, W. 1-Particle Properties of an Inhomogeneous Interacting Electron Gas Phys. Rev. 1966, 145, 561-567
82. Domingo, L. R.; Chamorro, E.; Perez, P. An Analysis of the Regioselectivity of 1,3-Dipolar Cycloaddition Reactions of Benzonitrile N-Oxides Based on Global and Local Electrophilicity and Nucleophilicity Indices Eur. J. Org. Chem. 2009, 3036-3044
83. Domingo, L. R.; Chamorro, E.; Perez, P. An Understanding of the Electrophilic/Nucleophilic Behavior of Electro-Deficient 2,3-Disubstituted 1,3-Butadienes in Polar Diels-Alder Reactions. A Density Functional Theory Study J. Phys. Chem. A 2008, 112, 4046-4053
84. Domingo, L. R.; Perez, P.; Saez, J. A. Understanding the Local Reactivity in Polar Organic Reactions Through Electrophilic and Nucleophilic Parr Functions RSC Adv. 2013, 3, 1486-1494
85. Chamorro, E.; Perez, P.; Domingo, L. R. On the Nature of Parr Functions to Predict the Most Reactive Sites Along Organic Polar Reactions Chem. Phys. Lett. 2013, 582, 141-143