Intramolecular cyclopropanation and C-H insertion reactions with metal carbenoids generated from cyclopropenes

Accounts of Chemical Research

Volumn 48, Issue 4, 2015, Pages 1021-1031

  Archambeau, Alexis ^a   Miege, Frédéric ^a   Meyer, Christophe ^a   Cossy, Janine ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84928339307     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00016     Document Type: Article

References (81)

1. Binger, P.; Büch, H. M. Cyclopropenes and Methylenecyclopropanes as Multifunctional Reagents in Transition Metal Catalyzed Reactions Top. Curr. Chem. 1987, 135, 77-151
2. Fox, J. M.; Yan, N. Metal Mediated and Catalyzed Nucleophilic Additions to Cyclopropenes Curr. Org. Chem. 2005, 9, 719-732
3. Rubin, M.; Rubina, M.; Gevorgyan, V. Recent Advances in Cyclopropene Chemistry Synthesis 2006, 1221-1245
4. Rubin, M.; Rubina, M.; Gevorgyan, V. Transition Metal Chemistry of Cyclopropenes and Cyclopropanes Chem. Rev. 2007, 107, 3117-3179
5. Marek, I.; Simaan, S.; Masarwa, A. Enantiomerically Enriched Cyclopropene Derivatives: Versatile Building Blocks in Asymmetric Synthesis Angew. Chem., Int. Ed. 2007, 46, 7364-7376
6. Miege, F.; Meyer, C.; Cossy, J. When Cyclopropenes Meet Gold Catalysts Beilstein J. Org. Chem. 2011, 7, 717-734
7. Zhu, Z.-B.; Wei, Y.; Shi, M. Recent Developments of Cyclopropene Chemistry Chem. Soc. Rev. 2011, 40, 5534-5563
8. Michaut, M.; Parrain, J.-L.; Santelli, M. Selective Ring Opening Cross Metathesis of Cyclopropenone Ketal: A One Step Synthesis of Protected Divinyl Ketones Chem. Commun. 1998, 2567-2568
9. Statsuk, A. V.; Liu, D.; Kozmin, S. A. Synthesis of Bistramide A J. Am. Chem. Soc. 2004, 126, 9546-9547
10. Singh, R.; Czekelius, C.; Schrock, R. R. Living Ring-Opening Metathesis Polymerization of Cyclopropenes Macromolecules 2006, 39, 1316-1317
11. Giudici, R. E.; Hoveyda, A. H. Directed Catalytic Asymmetric Olefin Metathesis. Selectivity Control by Enoate and Ynoate Groups in Ru-Catalyzed Asymmetric Ring-Opening/Cross-Metathesis J. Am. Chem. Soc. 2007, 129, 3824-3825
12. Miege, F.; Meyer, C.; Cossy, J. Ring-Rearrangement Metathesis of Cyclopropenes: Synthesis of Heterocycles Org. Lett. 2010, 12, 248-251
13. Seidel, G.; Mynott, R.; Fürstner, A. Elementary Steps of Gold Catalysis: NMR Spectroscopy Reveals the Highly Cationic Character of a "Gold Carbenoid" Angew. Chem., Int. Ed. 2009, 48, 2510-2513
14. Benitez, D.; Shapiro, N. D.; Tkatchouk, E.; Wang, Y.; Goddard, W. A., III; Toste, F. D. A Bonding Model for Gold(I) Carbene Complexes Nat. Chem. 2009, 1, 482-486
15. Cho, S. H.; Liebeskind, L. S. Practical Organic Synthesis with Strained-Ring Molecules. Rhodium-Catalyzed Carbonylation of Cyclopropenyl Esters and Cyclopropenyl Ketones to α-Pyrones and of Vinyl Cyclopropenes to Phenols J. Org. Chem. 1987, 52, 2631-2634
16. Padwa, A.; Xu, S. L. A New Phenol Synthesis from the Rhodium(I)-Catalyzed Reaction of Cyclopropenes and Alkynes J. Am. Chem. Soc. 1992, 114, 5881-5882
17. Shibata, T.; Maekawa, S.; Tamura, K. Rhodium-Catalyzed Intramolecular Cycloaddition of Cyclopropene-Ynes Triggered by Carbon-Carbon Bond Cleavage Heterocycles 2008, 76, 1261-1270
18. Li, C.; Zhang, H.; Feng, J.; Zhang, Y.; Wang, J. Rh(I)-Catalyzed Carbonylative Carbocyclization of Tethered Ene- and Yne-Cyclopropenes Org. Lett. 2010, 12, 3082-3085
19. Walker, J. A.; Orchin, M. Rearrangement of 1,2,3-Triphenylcyclopropene to 1,2-Diphenylindene Catalyzed by Di-Î-chlorodichlorobis(ethylene)diplatinum(II) Chem. Commun. 1968, 1239
20. Müller, P.; Pautex, N.; Doyle, M. P.; Bagheri, V. Rh(II)-Catalyzed Isomerizations of Cyclopropenes. Evidence for Rh(II)-Complexes Vinylcarbene Intermediates Helv. Chim. Acta 1990, 73, 1233-1241
21. II-Catalyzed Rearrangement of Cyclopropenes Helv. Chim. Acta 1993, 76, 521-534
22. Müller, P.; Gränicher, C. Selectivity in Rhodium(II)-Catalyzed Rearrangements of Cycloprop-2-ene-1-carboxylates Helv. Chim. Acta 1995, 78, 129-144
23. Zhu, Z.-B.; Shi, M. Gold(I)-Catalyzed Cycloisomerization of Arylvinylcyclopropenes: An Efficient Synthetic Protocol for the Construction of Indene Skeletons Chem. - Eur. J. 2008, 14, 10219-10222
24. Li, C.; Zeng, Y.; Wang, J. Au-Catalyzed Isomerization of Cyclopropenes: A Novel Approach to Indene Derivatives Tetrahedron Lett. 2009, 50, 2956-2959
25. 4-Catalyzed Cyclopropenation of Alkynes with Styryldiazoacetates J. Am. Chem. Soc. 2010, 132, 17211-17215
26. Davies, H. M. L.; Romines, K. R. Direct Synthesis of Furans by 3 + 2 Cycloaddition between Rhodium(II) Acetate Stabilized Carbenoids and Acetylenes Tetrahedron 1988, 44, 3343-3348
27. Padwa, A.; Kassir, J. M.; Xu, S. L. Rhodium-Catalyzed Ring-Opening Reaction of Cyclopropenes. Control of Regioselectivity by the Oxidation State of the Metal J. Org. Chem. 1991, 56, 6971-6972
28. Ma, S.; Zhang, J. 2,3,4- or 2,3,5-Trisubstituted Furans: Catalyst-Controlled Highly Regioselective Ring-Opening Cycloisomerization Reaction of Cyclopropenyl Ketones J. Am. Chem. Soc. 2003, 125, 12386-12387
29. Chen, J.; Ma, S. Catalyst-Controlled Ring-Opening Cycloisomerization Reactions of Cyclopropenyl Carboxylates for Highly Regioselective Synthesis of Different 2-Alkoxyfurans Chem. - Asian J. 2010, 5, 2415-2421
30. β,γ Butenolides from Allylic Cyclopropenecarboxylates via Tandem Ring Expansion/[3,3]-Sigmatropic Rearrangements Org. Lett. 2013, 15, 1500-1503
31. Bauer, J. T.; Hadfield, M. S.; Lee, A.-L. Gold Catalysed Reactions with Cyclopropenes Chem. Commun. 2008, 6405-6407
32. Chuprakov, S.; Gevorgyan, V. Regiodivergent Metal-Catalyzed Rearrangement of 3-Iminocyclopropenes into N -Fused Heterocycles Org. Lett. 2007, 9, 4463-4466
33. Hadfield, M. S.; Bauer, J. T.; Glen, P. E.; Lee, A.-L. Gold(I)-Catalysed Alcohol Additions to Cyclopropenes Org. Biomol. Chem. 2010, 8, 4090-4095
34. Mudd, R. J.; Young, P. C.; Jordan-Hore, J. A.; Rosair, G. M.; Lee, A.-L. Gold(I)-Catalyzed Addition of Thiols and Thioacids to 3,3-Disubstituted Cyclopropenes J. Org. Chem. 2012, 77, 7633-7639
35. Hadfield, M. S.; Lee, A.-L. Gold(I)-Catalysed Synthesis of Conjugated Trienes Chem. Commun. 2011, 47, 1333-1335
36. Young, P. C.; Hadfield, M. S.; Arrowsmith, L.; Macleod, K. M.; Mudd, R. J.; Jordan-Hore, J. A.; Lee, A.-L. Divergent Outcomes of Gold(I)-Catalyzed Indole Additions to 3,3-Disubstituted Cyclopropenes Org. Lett. 2012, 14, 898-901
37. Phan, D. T. H.; Dong, V. M. Silver-Catalyzed Ring-Opening of Cyclopropenes: Preparation of Tertiary α-Branched Allylic Amines Tetrahedron 2013, 69, 5726-5731
38. Doyle, M. P. Catalytic Methods for Metal Carbene Transformations Chem. Rev. 1986, 86, 919-939
39. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160
40. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; Wiley: New York, 1998.
41. Doyle, M. P.; Forbes, D. C. Recent Advances in Asymmetric Catalytic Metal Carbene Transformations Chem. Rev. 1998, 98, 911-935
42. Brookhart, M.; Studabaker, W. B. Cyclopropanes from Reactions of Transition-Metal-Carbene Complexes with Olefins Chem. Rev. 1987, 87, 411-432
43. Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Stereoselective Cyclopropanation Reactions Chem. Rev. 2003, 103, 977-1050
44. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Catalytic Carbene Insertion into C-H Bonds Chem. Rev. 2010, 110, 704-724
45. Doyle, M. P.; Ratnikov, M.; Liu, Y. Intramolecular Catalytic Asymmetric Carbon-Hydrogen Insertion Reactions. Synthetic Advantages in Total Synthesis in Comparison with Alternative Approaches Org. Biomol. Chem. 2011, 9, 4007-4016
46. Davies, H. M. L.; Beckwith, R. E. J. Catalytic Enantioselective C-H Activation by Metal-Carbenoid-Induced C-H insertion Chem. Rev. 2003, 103, 2861-2903
47. Davies, H. M. L.; Loe, Ø. Intermolecular C-H Insertions of Donor/Acceptor-Substituted Rhodium-Carbenoids: A Practical Solution for Catalytic Enantioselective C-H Activation Synthesis 2004, 2595-2608
48. Davies, H. M. L.; Morton, D. Guiding Principles for Site Selective and Stereoselective Intermolecular C-H Functionalization by Donor/Acceptor Rhodium Carbenes Chem. Soc. Rev. 2011, 40, 1857-1869
49. Davies, H. M. L.; Manning, J. R. Catalytic C-H Functionalization by Metal-Carbenoid and Nitrenoid Insertion Nature 2008, 451, 417-424
50. Binger, P.; McMeeking, J. Codimerization of 3,3-Dimethylcyclopropene with Ethylenecarboxylic Esters at Nickel(0) Catalysts Angew. Chem., Int. Ed. Engl. 1974, 13, 466-467
51. Tomilov, Y. V.; Borkadov, V. G.; Tsvetkova, N. M.; Dolgii, I. E.; Nefedov, O. M. Catalytic Vinylcarbene Isomerization of Cyclopropenes in the Presence of Olefins as a Method for Synthesizing Vinylcyclopropane Hydrocarbons Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1982, 31, 2129
52. Zhou, Y.; Trewyn, B. G.; Angelici, R. J.; Woo, L. K. Catalytic Reactions of Carbene Precursors on Bulk Gold Metal J. Am. Chem. Soc. 2009, 131, 11734-11743
53. Padwa, A.; Krumpe, K. E.; Gareau, Y.; Chiacchio, U. Rhodium(II)-Catalyzed Cyclization Reactions of Alkynyl-Substituted α-Diazo Ketones J. Org. Chem. 1991, 56, 2523-2530
54. 2] J. Org. Chem. 1990, 55, 4518-4520
55. Hoye, T. R.; Dinsmore, C. J. Rhodium(II) Acetate Catalyzed Alkyne Insertion Reactions of α-Diazo Ketones: Mechanistic Inferences J. Am. Chem. Soc. 1991, 113, 4343-4345
56. Padwa, A.; Blacklock, T. J.; Loza, R. Silver-Promoted Isomerizations of Some Cyclopropene Derivatives J. Am. Chem. Soc. 1981, 103, 2404-2405
57. Padwa, A.; Blacklock, T. J.; Loza, R. Mechanistic Aspects of the Silver(I)-Promoted Rearrangement of Cyclopropene Derivatives J. Org. Chem. 1982, 47, 3712-3721
58. Baird, M. S.; Hussain, H. H.; Nethercott, W. The Preparation and Lithiation of 1-Halogenocyclopropenes J. Chem. Soc., Perkin Trans. 1 1986, 1845-1853
59. Simaan, S.; Masarwa, A.; Zohar, E.; Stanger, A.; Bertus, P.; Marek, I. Cyclopropenylcarbinol Derivatives as New Versatile Intermediates in Organic Synthesis: Application to the Formation of Enantiomerically Pure Alkylidenecyclopropane Derivatives Chem. - Eur. J. 2009, 15, 8449-8464
60. Miege, F.; Meyer, C.; Cossy, J. Synthesis of 3-Oxa- and 3-Azabicyclo[4.1.0]heptanes by Gold-Catalyzed Cycloisomerization of Cyclopropenes Org. Lett. 2010, 12, 4144-4147
61. Hadfield, M. S.; Häller, L. J. L.; Lee, A.-L.; Macgregor, S. A.; O'Neill, J. A. T.; Watson, A. M. Computational Studies on the Mechanism of the Gold(I)-Catalysed Rearrangement of Cyclopropenes Org. Biomol. Chem. 2012, 10, 4433-4440
62. I Complex J. Org. Chem. 2013, 78, 9553-9559
63. Hon, Y.-S.; Chang, R.-C. The Studies of Carbenoid Reactions of α- O -Allyl- or α- N -Allyl-α′Diazopropanone Derivatives Catalyzed by Various Metal Ions Heterocycles 2008, 32, 1089-1099
64. Clark, J. S.; Dossetter, A. G.; Whittingham, W. G. Stereoselective Synthesis of the Bicyclic Core Structure of the Highly Oxidised Sesquiterpene Neoliacinic Acid Tetrahedron Lett. 1996, 37, 5605-5608
65. Miege, F.; Meyer, C.; Cossy, J. Gold(I)-Catalysed Cycloisomerisation of 1,6-Cyclopropene-Enes Chem. - Eur. J. 2012, 18, 7810-7822
66. 2-Catalyzed Cyclization of Dienynes-A Novel, Efficient, and Selective Synthesis of Carbocycles Angew. Chem., Int. Ed. 2002, 41, 2132-2135
67. Moreau, X.; Goddard, J.-P.; Bernard, M.; Lemière, G.; López-Romero, J. M.; Mainetti, E.; Marion, N.; Mouriès, V.; Thorimbert, S.; Fensterbank, L.; Malacria, M. Gold- vs. Platinum-Catalyzed Polycyclizations by O -Acyl Migration. Solvent-Free Reactions Adv. Synth. Catal. 2008, 350, 43-48
68. Watson, I. D. G.; Ritter, S.; Toste, F. D. Asymmetric Synthesis of Medium-Sized Rings by Intramolecular Au(I)-Catalyzed Cyclopropanation J. Am. Chem. Soc. 2009, 131, 2056-2057
69. Miege, F.; Meyer, C.; Cossy, J. Rhodium-Catalyzed Cycloisomerization Involving Cyclopropenes: Efficient Stereoselective Synthesis of Medium-Sized Heterocyclic Scaffolds Angew. Chem., Int. Ed. 2011, 50, 5932-5937
70. Kornecki, K. P.; Briones, J. F.; Boyarskikh, V.; Fullilove, F.; Autschbach, J.; Schrote, K. E.; Lancaster, K. M.; Davies, H. M. L.; Berry, J. F. Direct Spectroscopic Characterization of a Transitory Dirhodium Donor-Acceptor Carbene Complex Science 2013, 342, 351-354
71. Brooner, R. E. M.; Widenhoefer, R. A. Experimental Evaluation of the Electron Donor Ability of a Gold Phosphine Fragment in a Gold Carbene Complex Chem. Commun. 2014, 50, 2420-2425
72. Seidel, G.; Fürstner, A. Structure of a Reactive Gold Carbenoid Angew. Chem., Int. Ed. 2014, 53, 4807-4811
73. Hussong, M. W.; Rominger, F.; Krämer, P.; Straub, B. F. Isolation of a Non-Heteroatom-Stabilized Gold-Carbene Complex Angew. Chem., Int. Ed. 2014, 53, 9372-9375
74. Joost, M.; Estévez, L.; Mallet-Ladeira, S.; Miqueu, K.; Amgoune, A.; Bourissou, D. Enhanced π-Backdonation from Gold(I): Isolation of Original Carbonyl and Carbene Complexes Angew. Chem., Int. Ed. 2014, 53, 14152-14516
75. 3)-H Insertions with Donor Rhodium Carbenoids Generated from Cyclopropenes Angew. Chem., Int. Ed. 2012, 51, 11540-11544
76. Lee, E.; Choi, I.; Song, S. Y. Tertiary Alcohol Synthesis from Secondary Alcohols via C-H Insertion J. Chem. Soc., Chem. Commun. 1995, 321-322
77. Hansen, J.; Autschbach, J.; Davies, H. M. L. Computational Study on the Selectivity of Donor/Acceptor-Substituted Rhodium Carbenoids J. Org. Chem. 2009, 74, 6555-6563
78. Allinger, N. L.; Coke, J. L. The Relative Stabilities of cis and trans Isomers. VII. The Hydrindanes J. Am. Chem. Soc. 1960, 82, 2553-2556
79. Gordon, H. L.; Freeman, S.; Hudlicky, T. Stability Relationships in Bicyclic Ketones Synlett 2005, 2911-2914
80. Bililign, T.; Griffith, B. R.; Thorson, J. S. Structure, Activity, Synthesis and Biosynthesis of Aryl- C -Glycosides Nat. Prod. Rep. 2005, 22, 742-760
81. Shen, C.-C.; Cheng, J.-J.; Lay, H.-L.; Wu, S.-Y.; Ni, C.-L.; Teng, C.-M.; Chen, C.-C. Cytotoxic Apigenin Derivatives from Chrysopogon aciculatis J. Nat. Prod. 2012, 75, 198-201