Development of cascade reactions for the concise construction of diverse heterocyclic architectures

Accounts of Chemical Research

Volumn 45, Issue 8, 2012, Pages 1278-1293

  Lu, Liang Qiu ^a   Chen, Jia Rong ^a   Xiao, Wen Jing ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; SULFUR;

ARTICLE; CHEMISTRY; METHODOLOGY; RENEWABLE ENERGY;

ALKENES; CHEMISTRY; HETEROCYCLIC COMPOUNDS; INDOLES; RENEWABLE ENERGY; SULFUR;

EID: 84865343822     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar200338s     Document Type: Article

References (67)

1. Newman, D. J.; Cragg, G. M. Natural Products as Sources of New Drugs over the Last 25 Years J. Nat. Prod. 2007, 70, 461-477
2. Li, J. W.-H.; Vederas, J. C. Drug Discovery and Natural Products: End of an Era or an Endless Frontier? Science 2009, 325, 161-165
3. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer: New York, 1999; Vols. I-III.
4. Beller, M.; Bolm, C., Eds. Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals, 2 nd ed.; Wiley-VCH: Weinheim, Germany, 2004.
5. Berkessel, A.; Groeger, H. Asymmetric Organocatalysis; Wiley-VCH: Weinheim, Germany, 2005.
6. Special Issue: List, B. Organocatalysis Chem. Rev. 2007, 107, 5413-5883
7. MacMillan, D. W. C. The Advent and Development of Organocatalysis Nature 2008, 455, 304-308
8. Barbas, C. F., III Organocatalysis Lost: Modern Chemistry, Ancient Chemistry, and an Unseen Biosynthetic Apparatus Angew. Chem., Int. Ed. 2008, 47, 42-47
9. Muller, T. J. J., Ed. Metal Catalyzed Cascade Reactions; Topics in Organometallic Chemistry, Vol. 19; Springer: New York, 2006.
10. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Cascade Reactions in Total Synthesis Angew. Chem., Int. Ed. 2006, 45, 7134-7186
11. Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
12. Yu, X.-H.; Wang, W. Organocatalysis: Asymmetric Cascade Reactions Catalysed by Chiral Secondary Amines Org. Biomol. Chem. 2008, 6, 2037-2046
13. Nicolaou, K. C.; Chen, J. S. The Art of Total Synthesis through Cascade Reactions Chem. Soc. Rev. 2009, 38, 2993-3009
14. Grondal, C.; Jeanty, M.; Enders, D.; Hüttl, M. R. M. Organocatalytic Cascade Reactions as a New Tool in Total Synthesis Nature Chem. 2010, 2, 167-178
15. Narayanam, J. M. R.; Stephenson, C. R. J. Visible Light Photoredox Catalysis: Applications in Organic Synthesis Chem. Soc. Rev. 2011, 40, 102-113
16. Yoon, T. P.; Ischay, M. A.; Du, J. Visible Light Photocatalysis as a Greener Approach to Photochemical Synthesis Nat. Chem. 2010, 2, 527-532
17. Majumdar, K. C.; Chattopadhyay, S. K. Heterocycles in Natural Product Synthesis, 1 st ed.; Wiley-VCH: Weinheim, Germany, 2011.
18. Dua, R.; Shrivastava, S.; Sonwane., S. K.; Srivastava, S. K. Pharmacological Significance of Synthetic Heterocycles Scaffold: A Review Adv. Biol. Res. 2011, 5, 120-144
19. Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications, 2 nd ed.; Wiley-VCH: Weinheim, Germany, 2003.
20. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5 th ed.; Wiley-Blackwell: Chichester, U.K., 2010.
21. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Asymmetric Ylide Reactions: Epoxidation, Cyclopropanation, Aziridination, Olefination, and Rearrangement Chem. Rev. 1997, 97, 2341-2372
22. McGarrigle, E. M.; Myers, E. L.; Illa, O.; Shaw, M. A.; Riches, S. L.; Aggarwal, V. K. Chalcogenides as Organocatalysts Chem. Rev. 2007, 107, 5841-5883
23. Sun, X.-L.; Tang, Y. Ylide-Initiated Michael Addition-Cyclization Reactions beyond Cyclopropanes Acc. Chem. Res. 2008, 41, 937-948
24. Appel, R.; Hartmann, N.; Mayr, H. Scope and Limitations of Cyclopropanations with Sulfur Ylides J. Am. Chem. Soc. 2010, 132, 17894-17900
25. Feuer, H., Ed. Nitrile, Nitrones, and Nitronates in Organic Synthesis: Novel Strategies in Synthesis, 2 nd ed.; Wiley-VCH, Hoboken, NJ, 2007.
26. Lu, L.-Q.; Cao, Y.-J.; Liu, X.-P.; An, J.; Yao, C.-J.; Ming, Z.-H.; Xiao, W.-J. A New Entry to Cascade Organocatalysis: Reactions of Stable Sulfur Ylides and Nitroolefins Sequentially Catalyzed by Thiourea and DMAP J. Am. Chem. Soc. 2008, 47, 2489-2492
27. Denmark, S. E.; Thorarensen, A. Tandem [4 + 2]/[3 + 2] Cycloadditions of Nitroalkenes Chem. Rev. 1996, 96, 137-166
28. Lu, L.-Q.; Li, F.; An, J.; Zhang, J.-J.; An, X.-L.; Hua, Q.-L.; Xiao, W.-J. Construction of Fused Heterocyclic Architectures by Formal [4 + 1]/[3 + 2] Cycloaddition Cascade of Sulfur Ylides and Nitroolefins Angew. Chem., Int. Ed. 2009, 48, 9542-9545
29. Pandey, G.; Banerjee, P.; Gadre, S. R. Construction of Enantiopure Pyrrolidine Ring System via Asymmetric [3 + 2]-Cycloaddition of Azomethine Ylides Chem. Rev. 2006, 106, 4484-4517
30. A recent representative example, see: Zheng, J.-C.; Liao, W.-W.; Tang, Y.; Sun, X.-L.; Dai, L.-X. The Michael Addition-Elimination of Ylides to α,β-Unsaturated Imines. Highly Stereoselective Synthesis of Vinylcyclopropane-carbaldehydes and Vinylcyclopropylaziridines J. Am. Chem. Soc. 2005, 127, 12222-12223, and also please see other related references in ref 16
31. Lu, L.-Q.; Zhang, J.-J.; Li, F.; Cheng, Y.; Chen, J.-R.; Xiao, W.-J. Tuning Electronic and Steric Effects: Highly Enantioselective [4 + 1] Pyrroline Annulation of Sulfur Ylides with α,β-Unsaturated Imines Angew. Chem., Int. Ed. 2010, 49, 4495-4498
32. Lu, L.-Q.; Ming, Z.-H.; An, J.; Li, C.; Chen, J.-R.; Xiao, W.-J. Enantioselective Cascade Reactions of Stable Sulfur Ylides and Nitroolefins through an Axial-to-Central Chirality Transfer Strategy J. Org. Chem. 2012, 77, 1072-1080
33. 2-Symmetric Ureas J. Org. Chem. 2011, 76, 281-284
34. Lu, L.-Q.; Li, F.; An, J.; Cheng, Y.; Chen, J.-R.; Xiao, W.-J. Hydrogen-Bond-Mediated Asymmetric Cascade Reaction of Stable Sulfur Ylides with Nitroolefins: Scope, Application and Mechanism Chem.-Eur. J. 2012, 18, 4073-4079
35. Wang, X.-F.; Peng, L.; An, J.; Li, C.; Yang, Q.-Q.; Lu, L.-Q.; Gu, F.-L.; Xiao, W.-J. Enantioselective Intramolecular Crossed Rauhut-Currier Reactions through Cooperative Nucleophilic Activation and Hydrogen-Bonding Catalysis: Scope and Mechanistic Insight Chem.-Eur. J. 2011, 17, 6484-6491
36. Wang, X.-F.; Hua, Q.-L.; Cheng, Y.; An, X.-L.; Yang, Q.-Q.; Chen, J.-R.; Xiao, W.-J. Organocatalytic Asymmetric Sulfa-Michael/Michael Addition Reactions: A Strategy for the Synthesis of Highly Substituted Chromans with a Quaternary Stereocenter Angew. Chem., Int. Ed. 2010, 49, 8379-8383
37. Wang, X.-F.; An, J.; Zhang, X.-X.; Tan, F.; Chen, J.-R.; Xiao, W.-J. Catalytic Asymmetric Aza-Michael-Michael Addition Cascade: Enantioselective Synthesis of Polysubstituted 4-Amino-benzopyrans Org. Lett. 2011, 13, 808-811
38. Aroyan, C. E.; Dermenci, A.; Miller, S. J. Tetrahedron 2009, 65, 4069-4084
39. Marqués-López, E.; Herrera, R. P.; Marks, T.; Jacobs, W. C.; Könning, D.; de Figueiredo, R. M.; Christmann, M. Crossed Intramolecular Rauhut-Currier-Type Reactions via Dienamine Activation Org. Lett. 2009, 11, 4116-4119
40. Shen, H. C. Asymmetric Synthesis of Chiral Chromans Tetrahedron 2009, 65, 3931-3952
41. Bandini, M.; Umani-Ronchi, A. Catalytic Asymmetric Friedel-Crafts Alkylations; Wiley-VCH: Weinheim, Germany, 2009.
42. Bandini, M.; Eichholzer, A. Catalytic Functionalization of Indoles in a New Dimension Angew. Chem., Int. Ed. 2009, 48, 9608-9644
43. Samojłowicz, C.; Bieniek, M.; Grela, K. Ruthenium-Based Olefin Metathesis Catalysts Bearing N- Heterocyclic Carbene Ligands Chem. Rev. 2009, 109, 3708-3742
44. Alcaide, B.; Almendros, P.; Luna, A. Grubbs' Ruthenium-Carbenes beyond the Metathesis Reaction: Less Conventional Non-Metathetic Utility Chem. Rev. 2009, 109, 3817-3858
45. Yang, Q.; Xiao, W.-J.; Yu, Z.-K. Lewis Acid Assisted Ring-Closing Metathesis of Chiral Diallylamines: An Efficient Approach to Enantiopure Pyrrolidine Derivatives Org. Lett. 2005, 7, 871-874
46. Chen, J.-R.; Li, C.-F.; An, X.-L.; Zhang, J.-J.; Zhu, X.-Y.; Xiao, W.-J. Ru-Catalyzed Tandem Cross-Metathesis/Intramolecular Hydroarylation Sequence Angew. Chem., Int. Ed. 2008, 47, 2489-2492
47. An, X.-L.; Li, C.-F.; Zhang, F.-G.; Zou, Y.-Q.; Guo, Y.-C.; Chen, J.-R.; Xiao, W.-J. Highly Efficient Route to Functionalized Tetrahydrocarbazoles Using a Tandem Cross-Metathesis/Intramolecular-Hydroarylation Sequence Chem.-Asian J. 2010, 5, 2258-2265
48. Li, C.-F.; Liu, H.; Liao, J.; Cao, Y.-J.; Liu, X.-P.; Xiao, W.-J. Enantioselective Organocatalytic Intramolecular Ring-Closing Friedel-Crafts-Type Alkylation of Indoles Org. Lett. 2007, 9, 1847-1850
49. Lu, H.-H.; Liu, H.; Wu, W.; Wang, X.-F.; Lu, L.-Q.; Xiao, W.-J. Catalytic Asymmetric Intramolecular Hydroarylations of ω-Aryloxy- and Arylamino Tethered α,β-Unsaturated Aldehydes Chem.-Eur. J. 2009, 15, 2742-2746
50. Zhu, X.-Y.; An, X.-L.; Li, C.-F.; Zhang, F.-G.; Hua, Q.-L.; Chen, J.-R.; Xiao, W.-J. A Practical and Enantioselective Approach to Tetrahydrocarbazoles by Asymmetric Organocatalysis ChemCatChem 2011, 3, 679-683
51. Cai, Q.; Zhao, Z.-A.; You, S.-L. Asymmetric Construction of Polycyclic Indoles through Olefin Cross-Metathesis/Intramolecular Friedel-Crafts Alkylation under Sequential Catalysis Angew. Chem., Int. Ed. 2009, 48, 7428-7431
52. Ziegler, F. E.; Spitzner, E. B.; Wilkins, C. K. The Dimerization of 2-Vinylindoles and Their Alcohol Precursors J. Org. Chem. 1971, 36, 1759-1964
53. Pindur, U.; Eitel, M. New Regio- and Stereocontrolled Reactions of 2-Vinylindoles with CC-Dienophiles: Diels-Alder Reactions, Ene Reactions, and Michael Additions Heterocycles 1988, 27, 2353-2362
54. Chen, C.-B.; Wang, X.-F.; Cao, Y.-J.; Cheng, H.-G.; Xiao, W.-J. Brønsted Acid Mediated Tandem Diels-Alder/Aromatization Reactions of Vinylindoles J. Org. Chem. 2009, 74, 3532-3535
55. Wang, X.-F.; Cao, Y.-J.; Cheng, H.-G.; Chen, J.-R.; Xiao, W.-J. An Enantioselective Approach to Highly Substituted Tetrahydrocarbazoles through Hydrogen Bonding-Catalyzed Cascade Reactions Org. Lett. 2010, 12, 1140-1143
56. Tan, F.; Li, F.; Zhang, X.-X.; Wang, X.-F.; Cheng, H.-G.; Chen, J.-R.; Xiao, W.-J. Brønsted Acid Catalyzed Diels-Alder Reactions of 2-Vinylindoles and 3-Nitrocoumarins: An Expedient Synthesis of Coumarin-Fused Tetrahydrocarbazoles Tetrahedron 2011, 67, 446-451
57. Cao, Y.-J.; Cheng, H.-G.; Lu, L.-Q.; Zhang, J.-J.; Cheng, Y.; Chen, J.-R.; Xiao, W.-J. Organocatalytic Multiple Cascade Reactions: A New Strategy for the Construction of Enantioenriched Tetrahydrocarbazoles Adv. Synth. Catal. 2011, 353, 617-623
58. Cheng, H.-G.; Chen, C.-B.; Tan, F.; Chang, N.-J.; Chen, J.-R.; Xiao, W.-J. Convenient Synthesis of Tetrahydro-γ-carbolines and Tetrahydroquinolines through a Chemo- and Regioselectivity Switch by a Brønsted Acid Catalyzed, One-Pot, Multicomponent Reaction Eur. J. Org. Chem. 2010, 26, 4976-4980
59. Gioia, C.; Hauville, A.; Bernardi, L.; Fini, F.; Ricci, A. Organocatalytic Asymmetric Diels-Alder Reactions of 3-Vinylindoles Angew. Chem., Int. Ed. 2008, 47, 9236-9239
60. Jones, S. B.; Simmons, B.; MacMillan, D. W. C. Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine J. Am. Chem. Soc. 2009, 131, 13606-13607
61. Zheng, C.; Lu, Y.; Zhang, J.; Chen, X.; Chai, Z.; Ma, W.; Zhao, G. The Enantioselective, Organocatalyzed Diels-Alder Reaction of 2-Vinylindoles with α,β-Unsaturated Aldehydes: An Efficient Route to Functionalized Tetrahydrocarbazoles Chem.-Eur. J. 2010, 16, 5853-5857
62. Tan, B.; Hernandez-Torres, G.; Barbas, C. F., III Highly Efficient Hydrogen-Bonding Catalysis of the Diels-Alder Reaction of 3-Vinylindoles and Methyleneindolinones Provides Carbazo-lespirooxindole Skeletons J. Am. Chem. Soc. 2011, 133, 12354-12357
63. Fan, H.; Peng, J.; Hamann, M. T.; Hu, J. F. Lamellarins and Related Pyrrole-Derived Alkaloids from Marine Organisms Chem. Rev. 2008, 108, 264-287
64. Yu, C.; Zhang, Y.; Zhang, S.; Li, H.; Wang, W. Cu(II) Catalyzed Oxidation-[3 + 2] Cycloaddition-Aromatization Cascade: Efficient Synthesis of Pyrrolo[2,1-a]isoquinolines Chem. Commun. 2011, 47, 1036-1038
65. Zou, Y.-Q.; Lu, L.-Q.; Fu, L.; Chang, N.-J.; Rong, J.; Chen, J.-R.; Xiao, W.-J. Visible-Light-Induced Oxidation/[3 + 2] Cycloaddition/ OxidativeAromatization Sequence: A Photocatalytic Strategy To Construct Pyrrolo[2,1-a]isoquinolines Angew. Chem., Int. Ed. 2011, 50, 7171-7175
66. Xuan, J.; Cheng, Y.; An, J.; Lu, L.-Q.; Zhang, X.-X.; Xiao, W.-J. Visible Light-Induced Intramolecular Cyclization Reactions of Diamines: A New Strategy to Construct Tetrahydroimidazoles Chem. Commun. 2011, 47, 8337-8339
67. Zou, Y.-Q.; Chen, J.-R.; Liu, X.-P.; Lu, L.-Q.; Davis, R. L.; Jørgensen, K. A.; Xiao, W.-J. Highly Efficient Aerobic Oxidative Hydroxylation of Arylboronic Acids: Photoredox Catalysis Using Visible Light Angew. Chem., Int. Ed. 2012, 51, 784-788