Regioselective synthesis of 4- and 5-oxazole-phosphine oxides and -phosphonates from 2H-azirines and acyl chlorides

Tetrahedron

Volumn 60, Issue 40, 2004, Pages 8937-8947

  Palacios, Francisco ^a   Ochoa De Retana, Ana M ^a   Gil, José I ^a   Alonso, José M ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Acyl chloride; Azirine phosphine oxide and phosphonate; Oxazole

Indexed keywords

ACID; AZIRINE DERIVATIVE; CHLORIDE; OXAZOLE DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DERIVATIZATION; PRIORITY JOURNAL; RING CLOSING METATHESIS; RING OPENING; SYNTHESIS;

EID: 4444345503     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.07.013     Document Type: Article

References (82)

1. For recent reviews on azirines see: (a) F. Palacios, A.M. Ochoa de Retana, E. Martínez de Marigorta, and J.M. de los Santos Org. Prep. Proced. Int. 34 2002 219 269
2. T.L. Gilchrist Aldrichim. Acta 34 2001 51 55
3. B. Zwanenburg, and P. ten Holte Top. Cur. Chem. 216 2001 93 124
4. F. Palacios, A.M. Ochoa de Retana, E. Martínez de Marigorta, and J.M. de los Santos Eur. J. Org. Chem. 2001 2401 2414
5. H. Heimgartner Angew. Chem., Int. Ed. Engl. 30 1991 238 264
6. C.B. Bucher, and H. Heimgartner Helv. Chim. Acta 79 1996 1903 1915
7. J. Lehmann, A. Linden, and H. Heimgartner Tetrahedron 55 1999 5359 5376
8. B.C. Hong, A.K. Gupta, M.F. Wu, and J.H. Liao Tetrahedron Lett. 45 2004 1663 1666
9. S. Timen, and P. Somfai J. Org. Chem. 68 2003 9958 9963
10. T.M.V.D. Pinho e Melo, A.L. Cardoso, and A. d'A Rocha Gonzalves Tetrahedron 59 2003 2345 2351
11. T.M.V.D. Pinho e Melo, C.S.J. Lopes, A. d'A Rocha Gonzalves, J.A. Beja, A.M. Paixao, M.R. Silva, and L. Alte da Veiga J. Org. Chem. 67 2002 66 71
12. K. Banert, and F. Höhler Angew. Chem., Int. Ed. Engl. 40 2001 174 177
13. H.M.I. Osborn, and J. Sweeney Tetrahedron: Asymmetry 8 1997 1693 1715
14. D. Tanner Angew. Chem., Int. Ed. Engl. 33 1994 599 619
15. C. Xiong, W. Wang, C. Cai, and V.J. Hruby J. Org. Chem. 67 2002 1399 1402
16. S.N. Filigheddu, and M. Taddei Tetrahedron Lett. 39 1998 3857 3860
17. B. Zwanenburg, and L. Thijs Pure Appl. Chem. 68 1996 735 738
18. F.A. Davis, H. Liu, and C.V. Reddy Tetrahedron Lett. 37 1996 5473 5476
19. O. Ploux, M. Caruso, G. Chassaing, and A. Marquet J. Org. Chem. 53 1988 3154 3158
20. G. Righi, and R. D'Achielle Tetrahedron Lett. 37 1996 6893 6896
21. Y. Lim, and W.K. Lee Tetrahedron Lett. 36 1995 8431 8434
22. D. Tanner, C. Bergsson, and H.K. Dhaliwal Tetrahedron Lett. 31 1990 1903 1906
23. For reviews see: (a) Engel, R. Handbook of organophosphorus Chemistry, M. Dekker, Inc: New York, 1992. (b) Kafarski, P.; Lejczak, B. Phosphorus Sulfur 1991, 63, 193-215. (c) Hoagland, R. E.; Biologically Active natural Products Culter, H. G., Ed., ACS Symposium Series 380 American Chemical Society: Washington DC; 1988, 182. (d) Toy, A. D. F.; Walsh, E. N. Phosphorus Chemistry in Everyday Living, American Chemical Society: Washington DC, 1987 p 333.
24. For reviews see: (a) Engel, R. Handbook of organophosphorus Chemistry, M. Dekker, Inc: New York, 1992. (b) Kafarski, P.; Lejczak, B. Phosphorus Sulfur 1991, 63, 193-215. (c) Hoagland, R. E.; Biologically Active natural Products Culter, H. G., Ed., ACS Symposium Series 380 American Chemical Society: Washington DC; 1988, 182. (d) Toy, A. D. F.; Walsh, E. N. Phosphorus Chemistry in Everyday Living, American Chemical Society: Washington DC, 1987 p 333.
25. For reviews see: (a) Engel, R. Handbook of organophosphorus Chemistry, M. Dekker, Inc: New York, 1992. (b) Kafarski, P.; Lejczak, B. Phosphorus Sulfur 1991, 63, 193-215. (c) Hoagland, R. E.; Biologically Active natural Products Culter, H. G., Ed., ACS Symposium Series 380 American Chemical Society: Washington DC; 1988, 182. (d) Toy, A. D. F.; Walsh, E. N. Phosphorus Chemistry in Everyday Living, American Chemical Society: Washington DC, 1987 p 333.
26. For reviews see: (a) Engel, R. Handbook of organophosphorus Chemistry, M. Dekker, Inc: New York, 1992. (b) Kafarski, P.; Lejczak, B. Phosphorus Sulfur 1991, 63, 193-215. (c) Hoagland, R. E.; Biologically Active natural Products Culter, H. G., Ed., ACS Symposium Series 380 American Chemical Society: Washington DC; 1988, 182. (d) Toy, A. D. F.; Walsh, E. N. Phosphorus Chemistry in Everyday Living, American Chemical Society: Washington DC, 1987 p 333.
27. F. Palacios, A.M. Ochoa de Retana, J.I. Gil, and J.M. Ezpeleta J. Org. Chem. 65 2000 3213 3217
28. F. Palacios, A.M. Ochoa de Retana, and J.I. Gil Tetrahedron Lett. 41 2000 5363 5366
29. F. Palacios, A.M. Ochoa de Retana, and J. Pagalday Eur. J. Org. Chem. 2003 913 919
30. F. Palacios, D. Aparicio, J.M. de los Santos, and J. Vicario Tetrahedron 57 2001 1961 1972
31. F. Palacios, A.M. Ochoa de Retana, and J. Pagalday Tetrahedron 55 1999 14451 14458
32. F. Palacios, D. Aparicio, and J.M. de los Santos Tetrahedron 55 1999 13767 13778
33. F. Palacios, A.M. Ochoa de Retana, E. Martínez de Marigorta, M. Rodríguez, and J. Pagalday Tetrahedron 59 2003 2617 2623
34. F. Palacios, D. Aparicio, and J. Vicario Eur. J. Org. Chem. 2002 4131 4136
35. F. Palacios, A.M. Ochoa de Retana, and J. Oyarzabal Tetrahedron 55 1999 5947 5964
36. F. Palacios, D. Aparicio, A.M. Ochoa de Retana, J. García, and J. Oyarzabal Tetrahedron 55 1999 3105 3116
37. F. Palacios, J. Oyarzabal, S. Pascual, and A.M. Ochoa de Retana Org. Lett. 4 2002 769 772
38. F. Palacios, C. Alonso, P. Amezua, and G. Rubiales J. Org. Chem. 67 2002 1941 1946
39. F. Palacios, D. Aparicio, J. García, E. Rodríguez, and A. Fernández Tetrahedron 57 2001 3131 3141
40. F. Palacios, E. Herrán, and G. Rubiales J. Org. Chem. 64 1999 6239 6246
41. F. Palacios, A.M. Ochoa de Retana, S. Pascual, and R. López de Munain Tetrahedron Lett. 43 2002 5917 5920
42. F. Palacios, A.M. Ochoa de Retana, and J. Oyarzabal Tetrahedron 55 1999 3091 3104
43. J. Barluenga, F. López, and F. Palacios Tetrahedron Lett. 28 1987 2875 2876
44. F. Palacios, D. Aparicio, A.M. Ochoa de Retana, J.M. de los Santos, J.I. Gil, and R. López de Munain Tetrahedron: Asymmetry 14 2003 689 700
45. F. Palacios, A.M. Ochoa de Retana, J.I. Gil, and R. López de Munain Org. Lett. 4 2002 2405 2408
46. F. Palacios, D. Aparicio, A.M. Ochoa de Retana, J.M. de los Santos, J.I. Gil, and J.M. Alonso J. Org. Chem. 67 2002 7283 7288
47. F. Palacios, A.M. Ochoa de Retana, J.I. Gil, and J.M. Alonso Tetrahedron: Asymmetry 13 2002 2525 2541
48. F.W. Fowler, and A. Hassner J. Am. Chem. Soc. 90 1968 2875 2881
49. A. Hassner, S.S. Burke, and C. Jesse J. Am. Chem. Soc. 97 1975 4670 4692
50. H. Schmid, P. Gilgen, and H. Heimgartner Helv. Chim. Acta 57 1974 1393 1403
51. S. Sato, H. Kato, and M. Ohta Bull. Chem. Soc. Jpn 40 1967 2938 2942
52. U. Widmer, H. Heimgartner, and H. Schmid Helv. Chim. Acta 61 1978 815 821
53. E. Schaumamn, E. Kausch, and W. Walter Chem. Ber. 108 1975 2500 2509
54. For recent contributions see: (a) R.A. Miller, R.M. Smith, S. Karady, and R.A. Reamer Tetrahedron Lett. 43 2002 935 938
55. R. Berger, W.L. Shoop, J.V. Pivnichny, L.M. Warmke, M. Zakson-Aiken, K.A. Owens, P. de Montigny, D.M. Schamatz, M.J. Wyvratt, M.H. Fisher, P.T. Meinke, and S.L. Coletti Org. Lett. 3 2001 3715 3718
56. P. Wipf, and J.L. Methot Org. Lett. 3 2001 1261 1264
57. Z. Xia, and C.D. Smith J. Org. Chem. 66 2001 3459 3466
58. F. Yokokawa, T. Asano, and T. Shiori Tetrahedron 57 2001 6311 6327
59. A. Radspieler, and J. Liebscher Tetrahedron 57 2001 4867 4871
60. F. Yokokawa, T. Asano, and T. Shiori Org. Lett. 2 2000 4169 4172
61. M.C. Bagley, S.L. Hind, and C.J. Moody Tetrahedron Lett. 41 2000 6897 6900
62. For recent reviews on oxazoles see: (a) Lewis, J. R. Nat. Prod. Rep.2001, 18, 95-128. (b) Boyd, G. V. Prog. Heterocycl. Chem. 1999, 11, 213-229. (c) Lewis, J. R. Nat. Prod. Rep. 1998, 115, 417-437. (d) Comprehensive Heterocyclic Chemistry II; Hartner, F. W.; Katritzky, A. R.; Rees, C. W., Eds.; Elsevier: Oxford; 1996, Vol. 3, p. 261-318.
63. For recent reviews on oxazoles see: (a) Lewis, J. R. Nat. Prod. Rep.2001, 18, 95-128. (b) Boyd, G. V. Prog. Heterocycl. Chem. 1999, 11, 213-229. (c) Lewis, J. R. Nat. Prod. Rep. 1998, 115, 417-437. (d) Comprehensive Heterocyclic Chemistry II; Hartner, F. W.; Katritzky, A. R.; Rees, C. W., Eds.; Elsevier: Oxford; 1996, Vol. 3, p. 261-318.
64. For recent reviews on oxazoles see: (a) Lewis, J. R. Nat. Prod. Rep.2001, 18, 95-128. (b) Boyd, G. V. Prog. Heterocycl. Chem. 1999, 11, 213-229. (c) Lewis, J. R. Nat. Prod. Rep. 1998, 115, 417-437. (d) Comprehensive Heterocyclic Chemistry II; Hartner, F. W.; Katritzky, A. R.; Rees, C. W., Eds.; Elsevier: Oxford; 1996, Vol. 3, p. 261-318.
65. For recent reviews on oxazoles see: (a) Lewis, J. R. Nat. Prod. Rep.2001, 18, 95-128. (b) Boyd, G. V. Prog. Heterocycl. Chem. 1999, 11, 213-229. (c) Lewis, J. R. Nat. Prod. Rep. 1998, 115, 417-437. (d) Comprehensive Heterocyclic Chemistry II; Hartner, F. W.; Katritzky, A. R.; Rees, C. W., Eds.; Elsevier: Oxford; 1996, Vol. 3, p. 261-318.
66. For recent reviews see: (a) X.E. Hu Tetrahedron 60 2004 2701 2743
67. G. Cardillo, L. Gentilucci, and A. Tolomelli Aldrichim. Acta 36 2003 39 50
68. J.B. Sweeney Chem. Soc. Rev. 31 2002 247 258
69. For reviews see: (a) Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity. Kukhar, V. P., Hudson, H. R., Eds.; Wiley: Chichester, 2000. (b) Fields, S. F. Tetrahedron 1999, 55, 12237-12273. (c) Hiratake, J.; Oda, J. Biosci. Biotechnol. Biochem. 1997, 61, 211-218.
70. For reviews see: (a) Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity. Kukhar, V. P., Hudson, H. R., Eds.; Wiley: Chichester, 2000. (b) Fields, S. F. Tetrahedron 1999, 55, 12237-12273. (c) Hiratake, J.; Oda, J. Biosci. Biotechnol. Biochem. 1997, 61, 211-218.
71. For reviews see: (a) Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity. Kukhar, V. P., Hudson, H. R., Eds.; Wiley: Chichester, 2000. (b) Fields, S. F. Tetrahedron 1999, 55, 12237-12273. (c) Hiratake, J.; Oda, J. Biosci. Biotechnol. Biochem. 1997, 61, 211-218.
72. A.B. Smith, K.M. Yager, and C.M. Taylor J. Am. Chem. Soc. 117 1995 10879 10888
73. D.B. Smithrud, P.A. Benkovic, S.J. Benkovic, C.M. Taylor, K.M. Yager, J. Witherington, B.W. Phillips, P.A. Sprengler, A.B. Smith, and R. Hirschmann J. Am. Chem. Soc. 119 1997 278 282
74. R. Hirschmann, A.B. Smith, C.M. Taylor, P.A. Benkovic, S.D. Taylor, K.M. Yager, P.A. Spengler, and S.J. Benkovic Science 265 1994 234 237
75. J.H. Meyer, and P.A. Bartlett J. Am. Chem. Soc. 120 1998 4600 4609
76. S. Chackalamannil, S. Chung, A.W. Atamford, B.A. McKittrick, Y. Wang, H. Tsai, R. Cleven, A. Fawzi, and M. Czarniecki Bioorg. Med. Chem. Lett. 6 1996 1257 1260
77. J.A. Steere, P.B. Sampson, and J.F. Honek Bioorg. Med. Chem. Lett. 12 2002 457 460
78. H.J. Cristau, A. Cooulombeau, A. Genevis-Borella, and J.L. Pirat Tetrahedron Lett. 42 2001 4491 4494
79. D. Georgiadis, V. Dive, and A. Yiotakis J. Org. Chem. 66 2001 6604 6610
80. E.M. Wallace, J.A. Moliterni, M.A. Moskal, A.D. Neubart, N. Marcopulos, L.B. Stamford, A.J. Trapani, P. Savage, M. Chou, and A.Y. Jeng J. Med. Chem. 41 1998 1513 1523
81. S. Chen, and J.K. Coward J. Org. Chem. 63 1998 502 509
82. R. Hirschmann, K.M. Yager, C.M. Taylor, J. Witherington, P.A. Sprengler, B.W. Phillips, W. Moore, and A.B. Smith J. Am. Chem. Soc. 119 1997 8177 8190