Formation of P-Ylide under Neutral and Metal-Free Conditions: Transformation of Aziridines and Epoxides to Conjugated Dienes in the Presence of Phosphine

Journal of Organic Chemistry

Volumn 69, Issue 3, 2004, Pages 689-694

  Fan, Ren Hua ^a   Hou, Xue Long ^a   Dai, Li Xin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; METALS; PHOSPHORUS COMPOUNDS; SYNTHESIS (CHEMICAL);

AZIRIDINES;

ORGANIC COMPOUNDS;

ALKADIENE; AZIRIDINE DERIVATIVE; EPOXIDE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0842328953     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0354286     Document Type: Article

References (118)

1. (a) Wittig, G.; Schöllkopf, U. Chem. Ber. 1954, 87, 1318.
2. (b) Wittig, G. Angew. Chem. 1956, 68, 505.
3. (c) Organophosphorus Reagents in Organic Synthesis; Cadogan, J. I. G., Ed.; Academic Press: London, 1979.
4. (a) Dauben, W. G.; Kozikowski, A. P. Tetrahedron Lett. 1973, 3711.
5. (b) Dauben, W. G.; Hart, D. J.; Ipaktschi, J.; Kozikowski, A. P. Tetrahedron Lett. 1973, 4425.
6. (c) Organophosphorus Reagents in Organic Synthesis; Cadogan, J. I. G., Ed.; Academic Press: London, 1979.
7. (d) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
8. (e) Johnson, W. A. Ylides and Imines of Phosphorus; John Wiley & Sons: New York, 1993.
9. (f) Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1.
10. (g) Coyne, E.; Gilheany, D. G. In Comprehensive Organic Functional Group Transform; Katrizky, A. R., Meth-Cohn, O., Rees C. W., Eds.; Elsevier: Oxford, UK, 1995; Vol. 3.
11. (h) Kolodiazhny, O. I. Phosphorus Ylides; Wiley-VCH: Weinheim, 1999.
12. (i) Balema, V. P.; Wiench, J. W.; Pruski, M.; Pecharsky, V. K. J. Am. Chem. Soc. 2002, 124, 6244.
13. (a) Oda, R.; Kawabata, T.; Tanimoto S. Tetrahedron Lett. 1964, 1653.
14. (b) Burnett, M. G.; Oswald, T.; Walker, B. J. J. Chem. Soc. Chem. Commun. 1977, 155.
15. (c) Shi, L.; Wang, W.; Wang, Y.; Huang, Y. Z. J. Org. Chem. 1989, 54, 2028.
16. (d) Aggarwal, V. K. Synlett 1998, 329.
17. (e) Arisawa, K.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387.
18. (f) Aggarwal, V. K.; Alonso, E.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Porcelloni, M.; Studley, J. R. Angew. Chem., Int. Ed. 2001, 40, 1430.
19. (g) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrar, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1434.
20. (h) Aggarwal, V. K.; Ferrara, M.; O'Brien, C. J.; Thompson, A.; Jones, R. V. H.; Fieldhouse, R. J. Chem. Soc., Perkin Trans. 1 2001, 1635.
21. (i) Aggarwal, V. K.; de Vicente, J.; Bonnert, R. V. Org. Lett. 2001, 3, 2785.
22. (j) Lebel, H.; Paquet, V.; Proulx, C. Angew. Chem., Int. Ed. 2001, 40, 2887.
23. (k) Ye, S.; Tang, Y.; Dai, L. X. J. Org. Chem. 2001, 66, 5717.
24. (l) Huang, Z. Z.; Ye, S.; Xia, W.; Tang, Y. Chem. Commun. 2001, 1384.
25. (m) Balema, V. P.; Wiench, J. W.; Pruski, M.; Pecharsky, V. K. J. Am. Chem. Soc. 2002, 124, 6244.
26. (n) Ye, S.; Huang, Z. Z.; Xia, C. A.; Tang, Y.; Dai, L. X. J. Am. Chem. Soc. 2002, 124, 2432.
27. (o) Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747.
28. (p) Du, Y. S.; Lu, X. Y. Zhang, C. M. Angew. Chem., Int. Ed. 2003, 42, 1035.
29. (a) Singh, J.; Dhar, K. L.; Atal, C. K. Tetrahedron Lett. 1971, 2119.
30. (b) Henrick, C. A. Tetrahedron 1977, 33, 1845.
31. (c) Huang, Y. Z.; Shi, L. L.; Yang, J. H. Tetrahedron Lett. 1987, 28, 2159.
32. (d) Shi, L. L.; Xiao, W. J.; Yang, J. H.; Wen, X. Q.; Huang, Y. Z. Tetrahedron Lett. 1987, 28, 2155.
33. (e) Huang, Y. Z.; Shi, L. L.; Yang, J. H.; Cai, Z. W. J. Org. Chem. 1987, 52, 3558-3560.
34. (a) Ousset, J. B.; Mioskowski, C.; Solladie, G. Synth. Commun. 1983, 119.
35. (b) Schlosser, M.; Franzini, L. Synthesis 1998, 707.
36. (c) Wang, Q.; Wei, H. X.; Schlosser, M. Eur. J. Org. Chem. 1999, 3263, 3.
37. (d) Bartoli, G.; Dalpozzo, R.; Nino, A. D.; Procopio, A.; Sambri, L.; Tagarelli, A. Tetrahedron Lett. 2001, 42, 8833.
38. (e) Katritzky, A. R.; Denisko, O. V. J. Org. Chem. 2002, 67, 3104.
39. (f) Blackburn, L.; Pei, C. X.; Taylor, R. J. K. Synlett 2002, 215.
40. (g) Masuyama, Y.; Maekawa, K. Chem. Lett. 1988, 1449.
41. (h) Kurihara, T.; Kurusu, Y. Bull. Chem. Soc. Jpn. 1991, 64, 2311.
42. (i) Trost, B. M.; Kulawiec, R. J. J. Am. Chem. Soc. 1993, 115, 2027.
43. (a) Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7.
44. (b) Pattenden G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, p 223.
45. (c) Padwa, A.; Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 1a.
46. (d) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999.
47. For some reviews of syntheses and reactions of activated and unactivated aziridines, see: (a) Kasai, M.; Kono, M. Synlett 1992, 778.
48. (b) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
49. (c) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
50. (d) Rayner, C. M. Synlett 1997, 11.
51. (e) Ibuka, T. Chem. Soc. Rev. 1998, 27, 145.
52. (f) Li, A. H.; Dai, L. X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
53. (g) Stamm, H. J. Prakt. Chem. 1999, 319.
54. For some reviews of reactions of epoxides, see: (h) Pattenden, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, p 223.
55. (i) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361.
56. (j) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999.
57. (k) Willis, M. C. J. Chem. Soc., Perkin. Trans. 1 1999, 1765.
58. For some examples, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
59. (b) Stamm, H.; Baumnn, T. Pharmazie 1997, 52, 441.
60. (c) Muller, P.; Nury, P. Org. Lett. 1999, 1, 439.
61. (d) Li, Z.; Fernandez, M.; Jacobsen, E. N. Org. Lett. 1999, 1, 1611.
62. (e) Lee, W. Y.; Salvador, J. M.; Bodige, K. Org. Lett. 2000, 2, 931.
63. (f) Nakagawa, M.; Kawahara, M. Org. Lett. 2000, 2, 953.
64. (g) Gadikota, R. R.; Callam, C. S.; Lowary, T. L. J. Org. Chem. 2001, 66, 9046.
65. (h) Salomon, C. J. Synlett 2001, 65.
66. (i) Fringuelli, F.; Pizzo, F.; Vaccaro, L. Tetrahedron Lett. 2001, 42, 1131-1133.
67. (j) Ready, J. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 1374.
68. (k) Yadav, J. S.; Reddy, B. V. S.; Abraham, S.; Sabitha, G. Tetrahedron Lett. 2002, 43, 1565.
69. (l) Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. Org. Lett. 2002, 4, 2817.
70. (m) Hoard, D. W.; Moher, E. D.; Martinelli, M. J.; Norman, B. H. Org. Lett. 2002, 4, 1813-1815.
71. (n) Righi, P.; Scardovi, N.; Marotta, E.; ten Holte, P.; Zwanenburg, B. Org. Lett. 2002, 4, 497-500.
72. (o) Yadav, J. S.; Reddy, B. V. S.; Premalatha, K. Adv. Synth. Catal. 2003, 345, 948.
73. (p) Bisai, A.; Pandey, G.; Pandey, M. K.; Singh, V. K. Tetrahedron Lett. 2003, 44, 5839.
74. (a) Li, A. H.; Dai, L. X.; Hou, X. L.; Chen, M. B. J. Org. Chem. 1996, 61, 4641.
75. (b) Li, A. H.; Zhou, Y. G.; Dai, L. X.; Hou, X. L.; Xia, L. J.; Lin, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 1317.
76. (c) Hou, X. L.; Yang, X. F.; Dai, L. X. Chem. Commun. 1998, 747.
77. (d) Hou, X. L.; Wu, J.; Dai, L. X.; Xia, L. J.; Tang, M. H. Tetrahedron: Asymmetry 1998, 9, 1747.
78. (e) Hou, X. L.; Wu, J.; Dai, L.-X. Chinese J. Chem. 1998, 16, 557.
79. (f) Wu, J.; Hou, X. L.; Dai, L. X.; Xia, L. J.; Tang, M. H. Tetrahedron: Asymmetry 1998, 9, 3431.
80. (g) Zhou, Y. G.; Hou, X. L.; Dai, L. X.; Xia, L. J.; Tang, M. H. J. Chem. Soc., Perkin Trans. 1 1999, 77.
81. (h) Li, B. F.; Zhang, M. J.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2002, 67, 2902.
82. (i) Hou, X. L.; Fan, R. H.; Dai, L. X. J. Org. Chem. 2002, 67, 5295.
83. (j) Fan, R. H.; Hou, X. L. J. Org. Chem. 2003, 68, 726.
84. (k) Fan, R. H.; Hou, X. L. Tetrahedron Lett. 2003, 44, 4411.
85. (l) Fan, R. H.; Hou, X. L. Org. Biomol. Chem. 2003, 1, 1565.
86. (a) For reviews on the chemistry of phosphine, see: The Chemistry of Organophosphorus Compounds; Frank, H. R., Ed.; Wiley: West Sussex, 1990; Vol. 1.
87. (b) Christol, H.; Grelet, D.; Darvich, M. R.; Fallouh, F.; Plenat, F.; Cristau, H.-J. Bull. Soc. Chim. Fr. 1989, 477.
88. (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394.
89. (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819.
90. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906.
91. (f) Zhang, C.; Lu, X. Synlett 1995, 645.
92. (g) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461.
93. (h) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670.
94. (i) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031.
95. (j) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein.
96. (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876.
97. (l) Vedejs, E.; Rozners, E. J. Am. Chem. Soc. 2001, 123, 2428
98. (m) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett. 2001, 1499.
99. (n) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
100. (o) Wende, M.; Meier, R.; Gladysz, J. A. J. Am. Chem. Soc. 2001, 123, 11490.
101. (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
102. (q) Wang, L. C.; Luis, A. L.; Agapiou, K.; Jang, H. Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
103. (r) Lumbierres, M.; Moreno-MaLas, M.; Vallribera, A. Tetrahedron 2002, 58, 4061.
104. (s) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
105. (t) Wang, J. C.; Ng, S. S. Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682.
106. (u) Zhu, X. F.; Lan, J. Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716.
107. (v) Jellerichs, B. G.; Kong, J. R.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 7758.
108. (w) Vedejs, E.; Daugulis, O.; Harper, L. A.; MacKay, J. A. Powell, D. R. J. Org. Chem. 2003, 68, 5020.
109. Dellaria, J. F.; Sallin, K. J., Jr. Tetrahedron Lett. 1990, 2661.
110. Howard, R. W.; McDaniel, C. A.; Blomquist, G. J. J. Chem. Ecol. 1978, 4, 233.
111. Albright, T. A.; Freeman, W. J.; Schweizer, E. E. J. Am. Chem. Soc. 1975, 97, 2942.
112. Vedejs, E.; Snoble, K. A. J.; Fuchs, P. L. J. Org. Chem. 1973, 38, 1178.
113. Schweizer, E. E.; Smucker, L. D.; Votral, R. J. J. Org. Chem. 1966, 31, 467.
114. Ousset, J. B.; Mioskowski, C.; Solladie, G. Synth. Commun. 1983, 13, 1193.
115. Takaki, K.; Yasumura, M.; Negoro, K. J. Org. Chem. 1983, 48, 54.
116. Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1971, 93, 4070.
117. Tsukamoto, M.; Iio, H.; Tokoroyama, T. Tetrahedron Lett. 1987, 28, 4561.
118. Avery, T. D.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 5531.