The [3 + 3]-cycloaddition alternative for heterocycle syntheses: Catalytically generated metalloenolcarbenes as dipolar adducts

Accounts of Chemical Research

Volumn 47, Issue 4, 2014, Pages 1396-1405

  Xu, Xinfang ^a   Doyle, Michael P ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; HETEROCYCLIC COMPOUND; METAL; METHANE; TRANSITION ELEMENT;

ANALOGS AND DERIVATIVES; CATALYSIS; CHEMISTRY; CYCLOADDITION; PROCEDURES; SYNTHESIS;

CATALYSIS; CYCLOADDITION REACTION; HETEROCYCLIC COMPOUNDS; METALS; METHANE; TRANSITION ELEMENTS;

EID: 84898904712     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar5000055     Document Type: Article

References (91)

1. Lautens, M.; Klute, W.; Tam, W. Transition Metal-Mediated Cycloaddition Reactions Chem. Rev. 1996, 96, 49-92
2. Frühauf, H. Metal-Assisted Cycloaddition Reactions in Organotransition Metal Chemistry Chem. Rev. 1997, 97, 523-596
3. Huang, Y.; Lu, X. Novel Palladium Catalayzed Synthesis of Pyran Derivatives Tetrahedron Lett. 1987, 28, 6219-6220
4. Huang, Y.; Lu, X. Palladium Catalyzed Annulation Reaction Using a Bifunctional Allylic Alkylating Agent Tetrahedron Lett. 1988, 29, 5663-5664
5. Bambal, R. B.; Kemmitt, R. D.W. [3 + 3] Cycloaddition of Trimethylenemethane to Activated Aziridines: Palladium-catalysed Synthesis of Piperidines J. Organomet. Chem. 1989, 362, C18-C20
6. Schadw, W.; Reissig, H.-U. A New Diastereoselective Synthesis of Enantiomerically Pure 1,2-Oxazine Derivatives by Addition of Lithiated Methoxyallene to Chiral Nitrones Synlett 1999, 632-634
7. Helms, M.; Schade, W.; Pulz, R.; Watanabe, T.; Al-Harrasi, A.; Fisera, L.; Hlobilová, I.; Zahn, G.; Reissig, H.-U. Stereodivergent Syntheses of Highly Substituted Enantiopure 4-Alkoxy-3,6-dihydro-2 H -1,2-oxazines by Addition of Lithiated Alkoxyallenes to Carbohydrate-Derived Aldonitrones Eur. J. Org. Chem. 2005, 1003-1019
8. Al-Harrasi, A.; Reissig, H.-U. Synthesis of Enantiopure Carbohydrate Mimetics by Lewis Acid Catalyzed Rearrangement of 1,3-Dioxolanyl-Substituted 1,2-Oxazines Angew. Chem., Int. Ed. 2005, 44, 6227-6231
9. Hsung, R. P.; Shen, H. C.; Douglas, C. J.; Morgan, C. D.; Degen, S. J.; Yao, L. J. Sequential 1,2-Addition-Electrocyclic Ring Closures Involving Acyclic α,β-Unsaturated Iminiums: A Formal [3 + 3] Cycloaddition Strategy to Unique Pyranyl Spirocycles J. Org. Chem. 1999, 64, 690-691
10. Sklenicka, H. M.; Hsung, R. P.; Wei, L.; McLaughlin, M. J.; Gerasyuto, A. I.; Degen, S. J. Highly Stereoselective Formal [3 + 3] Cycloaddition Reactions of Chiral Vinylogous Amides with α,β-Unsaturated Iminiums Org. Lett. 2000, 2, 1161-1164
11. Hsung, R. P.; Kurdyumov, A. V.; Sydorenko, N. A Formal [3 + 3] Cycloaddition Approach to Natural-Product Synthesis Eur. J. Org. Chem. 2005, 23-44
12. Buchanan, G. S.; Feltenberger, J. B.; Hsung, R. P. Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis Curr. Org. Synth. 2010, 7, 363-401
13. Deng, J.; Wang, X.-N.; Hsung, R. P. A Formal [3 + 3] Cycloaddition Approach to Natural Product Synthesis. In Methods and Applications of Cycloaddition Reactions in Organic Syntheses; Nishiwaki, N., Ed.; Wiley-VCH: Weinheim, Germany, 2013, Chapter 12.
14. Na, R.; Jing, C.; Xu, Q.; Jiang, H.; Wu, X.; Shi, J.; Zhong, J.; Wang, M.; Benitez, D.; Tkatchouk, E.; Goddard, W. A.; Guo, H.; Kwon, O. Phosphine-Catalyzed Annulations of Azomethine Imines: Allene-Dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2+3] Pathways J. Am. Chem. Soc. 2011, 133, 13337-13348
15. Chan, A.; Scheidt, K. A. Highly Stereoselective Formal [3 + 3] Cycloaddition of Enals and Azomethine Imines Catalyzed by N-Heterocyclic Carbenes J. Am. Chem. Soc. 2007, 129, 5334-5335
16. Luo, S.; Zificsak, C. A.; Hsung, R. P. Intramolecular Formal Aza-[3 + 3] Cycloaddition Approach to Indoloquinolizidine Alkaloids. A Stereoselective Total Synthesis of (±)-Tangutorine Org. Lett. 2003, 5, 4709-4712
17. Cole, K. P.; Hsung, R. P. Intramolecular Formal oxa -[3 + 3] Cycloaddition Approach to the ABD System of Phomactin A Org. Lett. 2003, 5, 4843-4846
18. Sydorenko, N.; Hsung, R. P.; Darwish, O. S.; Hahn, J. M.; Liu, J. Tetronamides as Latent Acyclic Vinylogous Amides in Formal Aza -[3 + 3] Cycloaddition Reactions with α,β-Unsaturated Iminium Salts. An Unexpected Rearrangement and an Approach to Synthesis of Substituted Piperidines J. Org. Chem. 2004, 69, 6732-6738
19. Gerasyuto, A. I.; Hsung, R. P.; Sydorenko, N.; Slafer, B. A Formal [3 + 3] Cycloaddition Reaction. 5. An Enantioselective Intramolecular Formal Aza-[3 + 3] Cycloaddition Reaction Promoted by Chiral Amine Salts J. Org. Chem. 2005, 70, 4248-4256
20. Wang, Y.; Fang, D.; Liu, R. Theoretical Studies on Formal Hetero [3 + 3] Cycloaddition Reaction Between Vinylogous Amide and α,β-Unsaturated Imine Cation Tetrahedron 2005, 61, 5663-5669
21. Kurdyumov, A. V.; Lin, N.; Hsung, R. P.; Gullickson, G. C.; Cole, K. P.; Sydorenko, N.; Swidorski, J. J. A Lewis Acid-Catalyzed Formal [3 + 3] Cycloaddition of α,β-Unsaturated Aldehydes with 4-Hydroxy-2-pyrone, Diketones, and Vinylogous Esters Org. Lett. 2006, 8, 191-193
22. Luo, S.; Zhao, J.; Zhai, H. A Fast Assembly of Pentacyclic Benz[ f ]indolo[2,3- a ]quinolizidine Core by Tandem Intermolecular Formal Aza-[3 + 3] Cycloaddition/Pictet-Spengler Cyclization: A Formal Synthesis of (±)-Tangutorine J. Org. Chem. 2004, 69, 4548-4550
23. Hong, B.; Tseng, H.; Chen, S. Synthesis of Aromatic Aldehydes by Organocatalytic [4 + 2] and [3 + 3] Cycloaddition of α,β-Unsaturated Aldehydes Tetrahedron 2007, 63, 2840-2850
24. Hubert, C.; Moreau, J.; Batany, J.; Duboc, A.; Hurvois, J.; Renaud, J. Brønsted Acid-Catalyzed Synthesis of Pyrans via a Formal [3 + 3] Cycloaddition Adv. Synth. Catal. 2008, 350, 40-42
25. Sklenicka, H. M.; Hsung, R. P.; Wei, L.; McLaughlin, M. J.; Gerasyuto, A. I.; Degen, S. J. Highly Stereoselective Formal [3 + 3] Cycloaddition Reactions of Chiral Vinylogous Amides with α,β-Unsaturated Iminiums Org. Lett. 2000, 2, 1161-1164
26. Sklenicka, H. M.; Hsung, R. P.; McLaughlin, M. J.; Wei, L.; Gerasyuto, A. I.; Brennessel, W. B. Stereoselective Formal [3 + 3] Cycloaddition Approach to cis-1-Azadecalins and Synthesis of (-)-4a,8a-diepi-Pumiliotoxin C. Evidence for the First Highly Stereoselective 6π-Electron Electrocyclic Ring Closures of 1-Azatrienes J. Am. Chem. Soc. 2002, 124, 10435-10442
27. Movassaghi, M.; Chen, B. Stereoselective Intermolecular Formal [3 + 3] Cycloaddition Reaction of Cyclic Enamines and Enone Angew. Chem., Int. Ed. 2007, 46, 565-568
28. Hayashi, Y.; Gotoh, H.; Masui, R.; Ishikawa, H. Diphenylprolinol Silyl Ether as a Catalyst in an Enantioselective, Catalytic, Formal Aza [3 + 3] Cycloaddition Reaction for the Formation of Enantioenriched Piperidines Angew. Chem., Int. Ed. 2008, 47, 4012-4015
29. Hayashi, Y.; Toyoshima, M.; Gotoh, H.; Ishikawa, H. Diphenylprolinol Silyl Ether Catalysis in an Asymmetric Formal Carbo [3 + 3] Cycloaddition Reaction via a Domino Michael/Knoevenagel Condensation Org. Lett. 2009, 11, 45-48
30. Huang, J.; Zhao, L.; Liu, Y.; Cao, W.; Wu, X. Enantioselective Intermolecular Formal [3 + 3] Cycloaddition of 2,3-Disubstituted Indoles with Acrolein Org. Lett. 2013, 15, 4338-4341
31. Zhu, M.; Wei, Q.; Gong, L. Organocatalytic Asymmetric Formal [3 + 3] Cycloaddition Reactions of α,β-Unsaturated Aldehydes with Nazarov Reagents Adv. Synth. Catal. 2008, 350, 1281-1285
32. Harrity, J. P. A.; Provoost, O. [3 + 3] Cycloadditions and Related Strategies in Alkaloid Natural Product Synthesis Org. Biomol. Chem. 2005, 3, 1349-1358
33. Tang, Y.; Oppenheimer, J.; Song, Z.; You, L.; Zhang, X.; Hsung, R. P. Strategies and Approaches for Constructing 1-Oxadecalins Tetrahedron 2006, 62, 10785-10813
34. Lawrence, A. K.; Gademann, K. Aza-Annulation Strategies in Alkaloid Total Synthesis Synthesis 2008, 331-351
35. Hong, B.-C.; Wu, M.-F.; Tseng, H.-C.; Liao, J.-H. Enantioselective Organocatalytic Formal [3 + 3]-Cycloaddition of α,β-Unsaturated Aldehydes and Application to the Asymmetric Synthesis of (-)-Isopulegol Hydrate and (-)-Cubebaol Org. Lett. 2006, 8, 2217-2220
36. Cao, C.-L.; Sun, X.-L.; Kang, Y.-B.; Tang, Y. Enantioselective Formal [3 + 3] Annulation for the Direct Construction of Bicyclic Skeletons with Four Stereogenic Centers Org. Lett. 2007, 9, 4151-4154
37. 2/TFA- Promoted Formal [3 + 3] Cycloaddition/Oxidation of Enamines and Enones for Synthesis of Multisubstituted Aromatic Amines Org. Lett. 2012, 14, 3506-3509
38. Zhong, W.; Lin, F.; Chen, R.; Su, W. An Efficient Synthesis of 2-Hydroxy-7,8-dihydroquinolin-5(6 H)-ones and 7,8-Dihydroquinoline-2,5(1 H,6 H)-diones from Morita-Baylis-Hillman Adduct Acetates Synthesis 2008, 2561-2568
39. Pilipecz, M. V.; Varga, T. R.; Mucsi, Z.; Scheiber, P.; Nemes, P. [3 + 3] Cyclization Reactions of β-Nitroenamines and β-Enaminonitriles with α,β-Unsaturated Carboxylic Acid Chlorides Tetrahedron 2008, 64, 5545-5550
40. Alladoum, J.; Toum, V.; Hebbe, S.; Kadouri-Puchot, C.; Dechoux, L. Aza-annulation of β-Enaminolactones: Application to the Synthesis of Enantiopure Difunctionalized Bicyclic Lactams Tetrahedron Lett. 2009, 50, 617-619
41. Guo, H.; Xu, Q.; Kwon, O. Phosphine-Promoted [3 + 3] Annulations of Aziridines with Allenoates: Facile Entry into Highly Functionalized Tetrahydropyridines J. Am. Chem. Soc. 2009, 131, 6318-6319
42. Ye, L.-W.; Han, X.; Sun, X.-L.; Tang, Y. Tandem Michael Addition/Ylide Olefination Reaction for the Synthesis of Highly Functionalized Cyclohexadiene Derivatives Tetrahedron 2008, 64, 8149-8154
43. Ye, L.-W.; Wang, S.-B.; Wang, Q.-G.; Sun, X.-L.; Tang, Y.; Zhou, Y.-G. Asymmetric Tandem Michael Addition-Ylide Olefination Reaction for the Synthesis of Optically Active Cyclohexa-1,3-diene Derivatives Chem. Commun. 2009, 3092-3094
44. Shu, Z.; Zhu, J.; Liao, S.; Sun, X.; Tang, Y. Facile and Controllable Synthesis of Multiply Substituted Benzenes via a Formal [3 + 3] Cycloaddition Approach Tetrahedron 2013, 69, 284-292
45. Pattenden, L. C.; Wybrow, R. A. J.; Smith, S. A.; Harrity, J. P. A. A [3 + 3] Annelation Approach to Tetrahydropyridines Org. Lett. 2006, 8, 3089-3091
46. Manceya, N. C.; Butlinb, R. J.; Harrity, J. P. A. Investigation of a Tandem Iminium Ion Allylation Approach to Piperidines Synlett 2008, 17, 2647-2650
47. Wang, S.; Chai, Z.; Zhou, S.; Wang, S.; Zhu, X.; Wei, Y. A Novel Lewis Acid Catalyzed [3 + 3]-Annulation Strategy for the Syntheses of Tetrahydro-β-Carbolines and Tetrahydroisoquinolines Org. Lett. 2013, 15, 2628-2631
48. Fang, X.; Li, J.; Tao, H.; Wang, C. Highly Diastereoselective DABCO-Catalyzed [3 + 3]-Cycloaddition of 1,4-Dithiane-2,5-diol with Azomethine Imines Org. Lett. 2013, 15, 5554-5557
49. Dias, D. A.; Kerr, M. A. Domino Synthesis of Bridged Bicyclic Tetrahydro-1,2-oxazines: Access to Stereodefined 4-Aminocyclohexanols Org. Lett. 2009, 11, 3694-3697
50. Hu, B.; Zhu, J.; Xing, S.; Fang, J.; Du, D.; Wang, Z. A Highly Site-, Regio-, and Stereoselective Lewis Acid Catalyzed Formal [3 + 3] Cycloaddition of Methylenecyclopropane-1,1-Diesters with C, N -Diarylnitrones Chem.-Eur. J. 2009, 15, 324
51. Zhang, Y.; Liu, F.; Zhang, J. Catalytic Regioselective Control in the Diastereoselective 1,3-Dipolar Cycloaddition Reactions of 1-(1-Alkynyl) cyclopropyl Ketones with Nitrones Chem.-Eur. J. 2010, 16, 6146-6150
52. Gorbacheva, E. O.; Tabolin, A. A.; Novikov, R. A.; Khomutova, Y. A.; Nelyubina, Y. V.; Tomilov, Y. V.; Ioffe, S. L. Six-Membered Cyclic Nitronates as 1,3-Dipoles in Formal [3 + 3]-Cycloaddition with Donor-Acceptor Cyclopropanes. Synthesis of New Type of BicyclicNitrosoacetals Org. Lett. 2013, 15, 350-353
53. Shintani, R.; Hayashi, T. Palladium-Catalyzed [3 + 3] Cycloaddition of Trimethylenemethane with Azomethine Imines J. Am. Chem. Soc. 2006, 128, 6330-6331
54. Shapiro, N. D.; Shi, Y.; Toste, F. D. Gold-Catalyzed [3 + 3]-Annulation of Azomethine Imines with Propargyl Esters J. Am. Chem. Soc. 2009, 131, 11654-11655
55. Kanao, K.; Miyake, Y.; Nishibayashi, Y. Ruthenium-Catalyzed Enantioselective [3 + 3] Cycloaddition of Propargylic Alcohols with 2-Naphthols Organometalllics 2010, 29, 2126-2131
56. Grover, H. K.; Lebold, T. P.; Kerr, M. A. Tandem Cyclopropane Ring-Opening/Conia-ene Reactions of 2-Alkynyl Indoles: A [3 + 3] Annulative Route to Tetrahydrocarbazoles Org. Lett. 2011, 13, 220-223
57. 5 Shifts in Fischer Carbene Complexes: [4 + 3] and [3 + 3] Annulation Reactions of Furan and Pyrrole Rings J. Am. Chem. Soc. 1999, 121, 3065-3071
58. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons, Inc.: New York, 1998.
59. Wang, X.; Abrahams, Q. M.; Zavalij, P. Y.; Doyle, M. P. Highly Regio- and Stereoselective Dirhodium Vinylcarbene-induced Nitrone Cycloaddition with Subsequent Cascade Carbenoid Aromatic Cycloaddition/N-O Cleavage and Rearrangement Angew. Chem., Int. Ed. 2012, 51, 5907-5910
60. Xu, X.; Qian, Y.; Zavalij, P. Y.; Doyle, M. P. Highly Selective Catalyst-Dependent Competitive 1,2-C→C, -O→C, and -N→C Migrations from β-Methylene-β-silyloxy-β-amido-α-diazoacetates J. Am. Chem. Soc. 2013, 135, 1244-12447
61. Wang, X.; Xu, X.; Doyle, M. P. Asymmetric Formal [3 + 3] Cycloaddition Reactions of Nitrones with Electrophilic Vinylcarbene Intermediates J. Am. Chem. Soc. 2011, 133, 16402-16405
62. Pagar, V. V.; Jadhav, A. M.; Liu, R. Gold-Catalyzed Formal [3 + 3] and [4 + 2] Cycloaddition Reactions of Nitrosobenzenes with Alkenylgold Carbenoids J. Am. Chem. Soc. 2011, 133, 20728-20731
63. Wang, X.; Weigl, C.; Doyle, M. P. Solvent Enhancement of Reaction Selectivity: A Unique Property of Cationic Chiral Dirhodium Carboxamidates J. Am. Chem. Soc. 2011, 133, 9572-9579
64. 4-Catalyzed Enantioselective [3 + 2]-Cycloaddition between Nitrones and Vinyldiazoacetates J. Am. Chem. Soc. 2013, 135, 14516-14519
65. Xu, X.; Hu, W.-H.; Doyle, M. P. Divergent Outcomes from Catalysis by Dirhodium and Copper Separately or in Combination Angew. Chem., Int. Ed. 2011, 50, 11152-11355
66. Xu, X.; Ratnikov, M. O.; Zavalij, P. Y.; Doyle, M. P. Multifunctionalized 3-Hydroxypyrroles in a Three-Step, One-Pot Cascade Process from Methyl 3-TBSO-2-diazo-3-butenoate and Nitrones Org. Lett. 2011, 13, 6122-6125
67. Xu, X.; Zavalij, P. Y.; Doyle, M. P. Synthesis of Tetrahydropyridazines by a Metal-Carbene-Directed Enantioselective Vinylogous N-H Insertion/Lewis Acid-Catalyzed Diastereoselective Mannich Addition Angew. Chem., Int. Ed. 2012, 51, 9829-9833
68. Xu, B.; Zhu, S.; Xie, X.; Shen, J.; Zhou, Q. Asymmetric N-H Insertion Reaction Cooperatively Catalyzed by Rhodium and Chiral Spiro Phosphoric Acids Angew. Chem., Int. Ed. 2011, 50, 11483-11486
69. Zhu, S.; Zhou, Q. Transition-Metal-Catalyzed Enantioselective Heteroatom-Hydrogen Bond Insertion Reactions Acc. Chem. Res. 2012, 45, 1365-1377
70. Zhu, S.; Xu, B.; Wang, G.; Zhou, Q. Well-Defined Binuclear Chiral Spiro Copper Catalysts for Enantioselective N-H Insertion J. Am. Chem. Soc. 2012, 134, 436-442
71. Qian, Y.; Zavalij, P. J.; Hu, W.; Doyle, M. P. Bicyclic Pyrazolidinone Derivatives from Diastereoselective Catalytic [3 + 3]-Cycloaddition Reactions of Enoldiazoacetates with Azomethine Imines Org. Lett. 2013, 15, 1564-1567
72. Perreault, C.; Goudreau, S. R.; Zimmer, L. E.; Charette, A. B. Cycloadditions of Aromatic Azomethine Imines with 1,1-Cyclopropane Diesters Org. Lett. 2008, 10, 689-692
73. Zhou, Y.; Li, J.; Ling, L.; Liao, S.; Sun, X.; Li, Y.; Wang, L.; Tang, Y. Highly Enantioselective [3 + 3] Cycloaddition of Aromatic Azomethine Imines with Cyclopropanes Directed by π-π Stacking Interactions Angew. Chem., Int. Ed. 2013, 52, 1452-1456
74. Xu, X.; Zavalij, P. Y.; Doyle, M. P. Highly Enantioselective Dearomatizing Formal [3 + 3]-Cycloaddition Reactions of N -Acyliminopyridinium Ylides with Electrophilic Enolcarbene Intermediates Angew. Chem., Int. Ed. 2013, 52, 12664-12668
75. Xu, X.; Doyle, M. P. Enantiomer Recognition of Amides by Chiral Dirhodium(II) Carboxamidates Inorg. Chem. 2011, 50, 7610-7617
76. Allgäuer, D. S.; Mayer, P.; Mayr, H. Nucleophilicity Parameters of Pyridinium Ylides and Their Use in Mechanistic Analyses J. Am. Chem. Soc. 2013, 135, 15216-15224
77. Fernández, N.; Carrillo, L.; Vicario, J. L.; Badia, D.; Reyes, E. Organocatalytic Enantioselective (3 + 2) Cycloaddition Using Stable Azomethine Ylides Chem. Commun. 2011, 47, 12313-12315
78. Kucukdisli, M.; Opatz, T. A Modular Synthesis of Polysubstituted Indolizines Eur. J. Org. Chem. 2012, 4555-4564
79. Yang, Y.; Xie, C.; Xie, Y.; Zhang, Y. Synthesis of Functionalized Indolizines via Copper-Catalyzed Annulation of 2-Alkylazaarenes with α,β-Unsaturated Carboxylic Acids Org. Lett. 2012, 14, 957-959
80. Allgäuer, D. S.; Mayr, H. One-Pot Two-Step Synthesis of 1-(Ethoxycarbonyl)indolizines via Pyridinium Ylides Eur. J. Org. Chem. 2013, 6379-6388
81. Xu, X.; Zavalij, P. Y.; Doyle, M. P. Catalytic Asymmetric Syntheses of Quinolizidines by Dirhodium-Catalyzed Dearomatization of Isoquinolinium/ Pyridinium Methylides-The Role of Catalyst and Carbene Source J. Am. Chem. Soc. 2013, 135, 12439-12447
82. Qian, Y.; Xu, X.; Wang, X.; Zavalij, P. Y.; Hu, W.; Doyle, M. P. Rhodium(II)- and Copper(II)-Catalyzed Reactions of Enol Diazoacetates with Nitrones: Metal Carbene versus Lewis Acid Directed Pathways Angew. Chem., Int. Ed. 2012, 51, 5900-5903
83. Xu, X.; Zavalij, P. Y.; Hu, W.; Doyle, M. P. A Donor-Acceptor Cyclopropene as a Dipole Source for a Silver(I) Catalyzed Asymmetric Catalytic [3 + 3]-Cycloaddition with Nitrones Chem. Commun. 2013, 49, 10287-10289
84. Thompson, J. L.; Davies, H. M. L. Enhancement of Cyclopropanation Chemistry in the Silver-Catalyzed Reactions of Aryldiazoacetates J. Am. Chem. Soc. 2007, 129, 6090-6091
85. Urbano, J.; Braga, A. A. C.; Maseras, F.; álvarez, E.; Díaz-Requejo, M. M.; Péerez, P. J. The Mechanism of the Catalytic Functionalization of Haloalkanes by Carbene Insertion: An Experimental and Theoretical Study Organometallics 2009, 28, 5968-5981
86. Xu, X.; Shabashov, D.; Zavalij, P. Y.; Doyle, M. P. Unexpected Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides That Form 5-Arylaminofuran-2(3 H)-one-4-carboxylates Org. Lett. 2012, 14, 800-803
87. Xu, X.; Shabashov, D.; Zavalij, P. Y.; Doyle, M. P. Substrate-Dependent Divergent Outcomes from Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides: Azabicyclo[3.1.0]hexanes or 5-Arylaminofuran-2(3 H)-ones J. Org. Chem. 2012, 77, 5313-5317
88. Xu, X.; Zavalij, P. Y.; Hu, W.; Doyle, M. P. Efficient Synthesis of Oxazoles by Dirhodium(II)-catalyzed Reactions of Styryl diazoacetate with Oximes Chem. Commun. 2012, 48, 11522-11524
89. Truong, P. M.; Mandler, M. D.; Zavalij, P. Y.; Doyle, M. P. Tetrahydroquinolines and Benzazepines through Catalytic Diastereoselective Formal [4 + 2]-Cycloaddition Reactions between Donor-Acceptor Cyclopropenes and Imines Org. Lett. 2013, 15, 3278-3281
90. Xu, X.; Zavalij, P. Y.; Hu, W.; Doyle, M. P. Vinylogous Reactivity of Enol Diazoacetates with Donor-Acceptor Substituted Hydrazones. Synthesis of Substituted Pyrazole Derivatives J. Org. Chem. 2013, 78, 1583-1588
91. Xu, X.; Doyle, M. P. Recent Developments in the Synthetic Uses of Silyl-protected Enoldiazoacetates for Heterocyclic Syntheses Aust. J. Chem. 2013, 10.1071/CH13576