Highly selective synthesis of [(Z)-3-chloro-2-(phenylselanyl)-1-alkenyl] phosphonates and 2-ethoxy-4-(phenylselanyl)-2,5-dihydro-1,2-oxaphosphole 2-oxides by electrophilic reaction of 1,2-alkadienylphosphonates with PhSeCl

European Journal of Organic Chemistry

Volumn , Issue 1, 2010, Pages 101-110

  He, Guangke ^a   Yu, Yihua ^b   Fu, Chunling ^a   Ma, Shengming ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

Allenes; Cyclization; Electrophilic addition; Phosphorus; Selenium

Indexed keywords

EID: 73349141675     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900913     Document Type: Article

References (47)

1. H. Guo, R. Qian, Y. Guo, S. Ma, J. Org. Chem. 2008, 73, 7934-7938.
2. G. He, H. Guo, R. Qian, Y. Guo, C. Fu, S. Ma, Tetrahedron 2009, 65, 4877-4889.
3. For studies on allenyl sulfoxides and sulfones, see: a) S. Ma, Q. Wei, H. Wang, Org. Lett. 2000, 2, 3893-3895;
4. S. Ma, H. Ren, Q. Wei, J. Am. Chem. Soc. 2003, 125, 4817-4830;
5. G. He, C. Zhou, C. Fu, S. Ma, Tetrahedron 2007, 63, 3800-3805;
6. C. Zhou, C. Fu, S. Ma, Tetrahedron 2007, 63, 7612-7616;
7. C. Zhou, C. Fu, S. Ma, Angew. Chem. Int. Ed. 2007, 46, 4379-4381.
8. a) C. M. Angelov, T. N. Tancheva, Zh. Obshch. Khim. 1985, 55, 53-57;
9. D. M. Mondeshka, C. N. Eancheva, C. M. Angelov, Phosphorus Sulfur 1987, 31, 89-99.
10. R. S. Macomber, G. A. Krudy, K. Seff, L. E. Rendón- Diazmirón, J. Org. Chem. 1983, 48, 1425-1430.
11. For the electrophilic cyclization of allenylphosphonates, see: a) C. Tancheva, M. Bogilova, D. Mondeshka, Phosphorus Sulfur Silicon Relat. Elem. 2000, 157, 123-138;
12. J. Yuan, X. Ruan, Y. Yang, X. Huang, Synlett., 2007, 18, 2871-2874;
13. F. Yu, X. Lian, J. Zhao, Y. Yu, S. Ma, J. Org. Chem. 2009, 74, 1130-1134.
14. For the nucleophilic addition of allenylphosphonates with amines, imidazole, and thiols, see: a) N. G. Khusainova, O. A. Mostovaya, E. A. Berdnikov, I. A. Litvinov, D. B. Krivolapov, R. A. Cherkasov, Russ. J. Org. Chem. 2005, 41, 1260-1264;
15. N. G. Khusainova, E. A. Berdnikov, O. A. Mostovaya, S. M. Rybakov, R. A. Cherkasov, Russ. J. Org. Chem. 2007, 43, 1703-1705;
16. M. Chakravarty, K. C. K. Swamy, Synthesis 2007, 20, 3171-3178.
17. For phosphane-catalyzed annulations of allenylphosphonates, see: A. Panossian, N. Fleury-Brégeot, A. Marinetti, Eur. J. Org. Chem. 2008, 3826-3833.
18. For transition-metal-catalyzed reactions of allenylphosphonates or-phosphonic acid monoesters, see: a) H. Guo, Z. Zheng, F. Yu, S. Ma, Angew. Chem. Int. Ed. 2006, 45, 4997-5000;
19. S. Ma, F. Yu, J. Zhao, Synlett., 2007, 4, 583-586;
20. F. Yu, X. Lian, S. Ma, Org. Lett. 2007, 9, 1703-1706;
21. H. Guo, S. Ma, Adv. Synth. Catal. 2008, 350, 1213-1217.
22. a) S. Ma, Pure Appl. Chem. 2007, 79, 261-267;
23. S. Ma, Acc. Chem. Res. 2009, 1679-1688.
24. a) C. M. Angelov, C. Z. Christov, Synthesis 1984, 664-667;
25. D. D. Enchev, Heteroat. Chem. 2005, 16, 156-158.
26. int = 0.0227), number of observations [I2σ (I)]: 2707, parameters: 190. CCDC-739001 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
27. Z. Gu, Y. Deng, W. Shu, S. Ma, Adv. Synth. Catal. 2007, 349, 1653-1656.
28. a) S. Ma, X. Hao, X. Huang, Org. Lett. 2003, 5, 1217-1219;
29. S. Ma, X. Hao, X. Meng, X. Huang, J. Org. Chem. 2004, 69, 5720-5724;
30. S. Ma, X. Hao, X. Huang, Chem. Commun. 2003, 1082-1083.
31. Although we have not yet been able to realize such (Z)-selenochlorination for 1, 2-alkadienylphosphane oxides highly selectively, the formation of (Z)-selenochlorination products from allenylphosphane oxides as byproducts has been reported previously.[2]
32. a) T. Wirth, "Organoselenium Chemistry" in Topics in Current Chemistry 208, Springer, Heidelberg, 2000;
33. A. Krief in Comprehensive Organometallic Chemistry II (Eds.: E. V. Abel, F. G. A. Stone, G. Wilkinson), Pergamon Press, New York, 1995, vol. 11, chapter 13;
34. C. Paulmier, "Selenium Reagents and Intermediates in Organic Synthesis" in Organic Chemistry Series 4 (Ed.: J. E. Baldwin), Pergamon Press, Oxford, 1986.
35. a) C. W. Nogueira, G. Zeni, J. B. T. Rocha, Chem. Rev. 2004, 104, 6255-6285;
36. G. Mugesh, W. du Mont, H. Sies, Chem. Rev. 2001, 101, 2125-2179;
37. M. J. Parnham, E. Graf, Prog. Drug Res. 1991, 36, 9-47;
38. C. W. Nogueira, E. B. Quinhones, E. A. C. Jung, G. Zeni, J. B. T. Rocha, Inflammation Res. 2003, 52, 56-63.
39. a) J. V. Comasseto, N. Petragnani, J. Organomet. Chem. 1978, 152, 295-304;
40. J. V. Comasseto, L. W. Ling, N Petragnani, H. A. Stefani, Synthesis 1997, 373-403;
41. J. V. Comasseto, J. Organomet. Chem. 1983, 253, 131-181;
42. G. Perin, E. J. Lenardão, R. G. Jacob, R. B. Panatieri, Chem. Rev. 2009, 109, 1277-1301.
43. a) T. Minami, J. Motoyoshiya, Synthesis 1992, 333-349;
44. R. Engel, Chem. Rev. 1977, 77, 349-367;
45. R. R. Breaker, G. R. Gough, P. T. Gilham, Biochemistry 1993, 32, 9125-9128;
46. M. R. Harnden, A. Parkin, M. J. Parratt, R. M. Perkins, J. Med. Chem. 1993, 36, 1345-1355.
47. H. Altenbach, R. Korff, Tetrahedron Lett. 1981, 22, 5175-5178.