Organocatalytic hetero [4+2] cycloaddition reactions of 2-(1-alkynyl)-2-alkene-1-ones: Metal-free access to highly substituted 4H-pyrans

Organic and Biomolecular Chemistry

Volumn 8, Issue 22, 2010, Pages 5059-5061

  Yu, Xiuzhao ^a   Cao, Zhongyan ^a   Zhang, Junliang ^a,b  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

[4+2] CYCLOADDITION REACTIONS; ALKYNYLS; FREE ACCESS; HETERODIENES; ORGANOCATALYTIC;

CYCLOADDITION;

OLEFINS;

ALKENE; METAL; PYRAN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; CONFORMATION; CYCLIZATION;

ALKENES; CATALYSIS; CYCLIZATION; METALS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; PYRANS;

EID: 78049324406     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00334d     Document Type: Article

References (55)

1. E. Quinoa Y. Kakou P. Crews J. Org. Chem. 1988 53 3642
2. D. G. Corley R. Herb R. E. Moore P. J. Scheuer V. J. Paul J. Org. Chem. 1988 53 3644
3. S. Hatakeyama N. Ochi H. Numata S. Takano J. Chem. Soc., Chem. Commun. 1988 1202
4. R. Gonzalez N. Martin C. Seoane J. L. Marco A. Albert F. H. Cano Tetrahedron Lett 1992 33 3809
5. R. D. Norcross I. Paterson Chem. Rev. 1995 95 2041
6. C. W. Jefford G. Bernardinelli J. Tanaka T. Higa Tetrahedron Lett. 1996 37 159
7. D. J. Faulkner Nat. Prod. Rep. 2000 17 7
8. H. Hayakawa M. Miyashita Tetrahedron Lett. 2000 41 707
9. M. M. Faul B. E. Huff Chem. Rev. 2000 100 2407
10. I. Paterson C. De, savi M. Tudge Org. Lett. 2001 3 3149
11. W. R. Roush G. J. Dilley Synlett 2001 955
12. Y. Kishi Pure Appl. Chem. 1998 70 339
13. G. Pattenden M. A. González P. B. Little D. S. Millan A. T. Plowright J. A. Tornos T. Ye Org. Biomol. Chem. 2003 1 4173
14. L. O. Haustedt I. V. Hartung H. M. R. Hoffmann Angew. Chem., Int. Ed. 2003 42 2711
15. Z. Xu W. W. Barrow W. J. Suling L. Westbrook E. Barrow Y. Lina M. T. Flavin Bioorg. Med. Chem. 2004 12 1199
16. B. S. Lucas V. Gopalsamuthiram S. D. Burke Angew. Chem., Int. Ed. 2007 46 769
17. L. J. Van Orden B. D. Patterson S. D. Rychnovsky J. Org. Chem. 2007 72 5784
18. 4H-Pyrans are bioactive compounds, see: K. Urbahns E. HorvNth J.-P. Stasch F. Mauler Bioorg. Med. Chem. Lett. 2003 13 2637 and references cited therein.
19. I. Larrosa P. Romea F. Urpí Tetrahedron 2008 64 2683
20. G. W. O'Neil A. Fürstner Chem. Commun. 2008 4294
21. M. Toshiya K. Tsutomu I. Takashi Y. Hiroki Chem. Lett. 2000 6 666
22. D. Kumar V. B. Reddy S. Sharad U. Dube S. Kapur Eur. J. Med. Chem. 2009 44 3805
23. R. I. Jr. Longley W. S. Emerson J. Am. Chem. Soc. 1950 72 3079
24. D. L. Boger K. D. Robarge J. Org. Chem. 1988 53 3377
25. L. F. Tietze T. Hübsch E. Voss M. Buback W. Tost J. Am. Chem. Soc. 1988 110 4065
26. L. F. Tietze C. Schneider A. Montenbruck Angew. Chem., Int. Ed. Engl. 1994 33 980
27. L. F. Tietze G. Kettschau Top. Curr. Chem. 1997 189 1
28. L. F. Tietze G. Kettschau J. A. Gewart A. Schuffenhauer Curr. Org. Chem. 1998 2 19
29. J. Thorhauge M. Johannsen K. A. Jørgensen Angew. Chem., Int. Ed. 1998 37 2404
30. D. A. Evans J. S. Johnson J. Am. Chem. Soc. 1998 120 4895
31. K. A. Jørgensen Angew. Chem. Int. Ed. 2000 39 3558
32. K. Gademann D. E. Chavez E. N. Jacobsen Angew. Chem., Int. Ed. 2002 41 3059
33. K. Juhl K. A. Jørgensen Angew. Chem., Int. Ed. 2003 42 1498
34. F. Yi Y. Peng G. Song Tetrahedron Lett. 2005 46 3931
35. H. Waldmann V. Khedkar H. Dückert M. Schürmann I. M. Oppel K. Kumar Angew. Chem., Int. Ed. 2008 47 6869
36. J. Ficíní A. Krief Tetrahedron Lett. 1970 11 885
37. C. P. Dell Tetrahedron Lett. 1992 33 699
38. R. P. Hsung C. A. Zificsak L.-L. Wei C. J. Douglas H. Xiong J. A. Mulder Org. Lett. 1999 1 1237
39. T. Mantani T. Konno T. Ishihara H. Yamanaka Chem. Lett. 2000 666
40. B. M. Trost R. E. Brown F. D. Toste J. Am. Chem. Soc. 2000 122 5877
41. I. Koyama T. Kurahashi S. Matsubara J. Am. Chem. Soc. 2009 131 1350
42. Y. Xiao J. Zhang Angew. Chem., Int. Ed. 2008 47 1903
43. X. Yu H. Ren Y. Xiao J. Zhang Chem.-Eur. J. 2008 14 8481
44. L. Fan W. Zhao W. Jiang J. Zhang Chem.-Eur. J. 2008 14 9139
45. Y. Xiao J. Zhang Adv. Synth. Catal. 2009 351 617
46. Y. Zhang Z. Chen Y. Xiao J. Zhang Chem.-Eur. J. 2009 15 5208
47. Y. Xiao J. Zhang Chem. Commun. 2009 3594
48. F. Liu J. Zhang Angew. Chem., Int. Ed. 2009 48 5505
49. H. Gao X. Zhao Y. Yu J. Zhang Chem.-Eur. J. 2010 16 456
50. Y. Xiao J. Zhang Chem. Commun. 2010 46 752
51. For transition-metal catalyzed or electrophiles mediated cyclization, please see: T. Yao X. Zhang R. C. Larock J. Am. Chem. Soc. 2004 126 11164
52. T. Yao X. Zhang R. C. Larock J. Org. Chem. 2005 70 7679
53. Y. H. Liu S. Zhou Org. Lett. 2005 7 4609
54. N. T. Patil H. Wu Y. Yamamoto J. Org. Chem. 2005 70 4531
55. CCDC 738752 (2b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge form The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.