Intramolecular generation and rearrangement of oxonium ylides: Methodology studies and their application in synthesis

Tetrahedron

Volumn 69, Issue 13, 2013, Pages 2667-2686

  Murphy, Graham K ^a   Stewart, Craig ^b   West, F G ^b  

^a UNIVERSITY OF WATERLOO   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CARBENOID; CARBONYL DERIVATIVE; COPPER; ELECTROPHILE; GRISEOFULVIN; ION; LAULIMALIDE; MACROCYCLIC COMPOUND; NITROGEN; OXONIUM YLIDE; OXYGEN DERIVATIVE; PHOSPHORUS; SULFONAMIDE; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CONFORMATION; CYCLOPROPANATION; DECOMPOSITION; ELECTRON; METHODOLOGY; MOLECULAR DYNAMICS; MOLECULAR STABILITY; NUCLEOPHILICITY; PHOTOLYSIS; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; STEVENS REARRANGEMENT; SYNTHESIS;

EID: 84874303999     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.01.051     Document Type: Review

References (101)

1. M.P. Doyle, M.A. Mckervey, and T. Ye Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cycloproapanes to Ylides 1998 Wiley-Interscience p 652
2. A. Padwa, and K.E. Krumpe Tetrahedron 48 1992 5385
3. J.B. Sweeney Chem. Soc. Rev. 38 2009 1027
4. G. Mehta, and S. Muthusamy Tetrahedron 58 2002 9477
5. A. Padwa, and E.A. Curtis Arkivoc 2 2001 1043
6. A. Padwa, Z.J.J. Zhang, and L. Zhi J. Org. Chem. 65 2000 5223
7. M.A. Garcia-Garibay, and H. Dang Org. Biomol. Chem. 7 2009 1106
8. J.P. Cheng, B. Liu, Y.Y. Zhao, Y.K. Sun, X.M. Zhang, and Y. Lu J. Org. Chem. 64 1999 604
9. G.A. Olah, H. Doggweiler, and J.D. Felberg J. Org. Chem. 49 1984 2112
10. G.A. Olah, H. Doggweiler, and J.D. Felberg J. Org. Chem. 49 1984 2116
11. G.A. Olah, H. Doggweiler, J.D. Felberg, S. Frohlich, M.J. Grdina, R. Karpeles, T. Keumi, S. Inaba, W.M. Ip, K. Lammertsma, G. Salem, and D.C. Tabor J. Am. Chem. Soc. 106 1984 2143
12. J.S. Clark Nitrogen, Oxygen and Sulfur Ylide Chemistry 2002 Oxford
13. H. Nozaki, H. Takaya, and R. Noyori Tetrahedron Lett. 1965 2563
14. H. Nozaki, H. Takaya, and R. Noyori Tetrahedron 22 1966 3393
15. W. Ando, H. Yamato, H. Kohoda, T. Migita, S. Kondo, K. Ichibori, I. Imai, S. Nakaido, and K. Nakayama J. Am. Chem. Soc. 94 1972 3870
16. K. Friedrich, U. Jansen, and W. Kirmse Tetrahedron Lett. 26 1985 193
17. W. Kirmse, P. Vanchiem, and V. Schurig Tetrahedron Lett. 26 1985 197
18. T.S. Stevens, E.M. Creighton, A.B. Gordon, and M. Macnicol J. Chem. Soc. 1928 3193
19. J. Adams, and R. Frenette Tetrahedron Lett. 28 1987 4773
20. J. Adams, M.A. Poupart, L. Grenier, C. Schaller, N. Ouimet, and R. Frenette Tetrahedron Lett. 30 1989 1749
21. J. Adams, and D.M. Spero Tetrahedron 47 1991 1765
22. M.C. Pirrung, and J.A. Werner J. Am. Chem. Soc. 108 1986 6060
23. E.J. Roskamp, and C.R. Johnson J. Am. Chem. Soc. 108 1986 6062
24. W.D. Ollis, M. Rey, and I.O. Sutherland J. Chem. Soc., Perkin Trans. 1 1983 1009
25. N.P. Karche, S.M. Jachak, and D.D. Dhavale J. Org. Chem. 66 2001 6323
26. T.H. Eberlein, F.G. West, and R.W. Tester J. Org. Chem. 57 1992 3479
27. M.C. Pirrung, W.L. Brown, S. Rege, and P. Laughton J. Am. Chem. Soc. 113 1991 8561
28. F.G. West, B.N. Naidu, and R.W. Tester J. Org. Chem. 59 1994 6892
29. V.N. Desai, N.N. Saha, and D.D. Dhavale J. Chem. Soc., Perkin Trans. 1 2000 147
30. T. Yakura, K. Matsui, K. Matsuzaka, and M. Yamashita Heterocycles 79 2009 353
31. K.L. Jackson, J.A. Henderson, H. Motoyoshi, and A.J. Phillips Angew. Chem., Int. Ed. 48 2009 2346
32. J.S. Clark, G. Whitlock, S. Jiang, and N. Onyia Chem. Commun. 2003 2578
33. M.P. Moyer, P.L. Feldman, and H. Rapoport J. Org. Chem. 50 1985 5223
34. D.F. Taber, and E.H. Petty J. Org. Chem. 47 1982 4808
35. W. Kirmse, and K. Kund J. Am. Chem. Soc. 111 1989 1465
36. A. Padwa, S.F. Hornbuckle, G.E. Fryxell, and P.D. Stull J. Org. Chem. 54 1989 817
37. F.P. Marmsater, J.A. Vanecko, and F.G. West Org. Lett. 6 2004 1657
38. M.P. Doyle, V. Bagheri, and E.E. Claxton J. Chem. Soc., Chem. Commun. 1990 46
39. H. Nozaki, H. Takaya, S. Moriuti, and R. Noyori Tetrahedron 24 1968 3655
40. J.S. Clark Tetrahedron Lett. 33 1992 6193
41. J.S. Clark, S.A. Krowiak, and L.J. Street Tetrahedron Lett. 34 1993 4385
42. D.M. Hodgson, F.Y.T.M. Pierard, and P.A. Stupple Chem. Soc. Rev. 30 2001 50
43. J.B. Lambert, and D.H. Johnson J. Am. Chem. Soc. 90 1968 1349
44. F.G. West, T.H. Eberlein, and R.W. Tester J. Chem. Soc., Perkin Trans. 1 1993 2857
45. W. Ando Acc. Chem. Res. 10 1977 179
46. M.P. Doyle, W.H. Tamblyn, and V. Bagheri J. Org. Chem. 46 1981 5094
47. J.S. Clark, T.C. Fessard, and G.A. Whitlock Tetrahedron 62 2006 73
48. F.P. Marmsater, and F.G. West J. Am. Chem. Soc. 123 2001 5144
49. K.S. Feldman, and M.L. Wrobleski J. Org. Chem. 65 2000 8659
50. G.K. Murphy, F.P. Marmsater, and F.G. West Can. J. Chem. 84 2006 1470
51. G.K. Murphy, and F.G. West Org. Lett. 7 2005 1801
52. M.P. Doyle, D.G. Ene, D.C. Forbes, and J.S. Tedrow Tetrahedron Lett. 38 1997 4367
53. D.M. Jaber, R.N. Burgin, M. Helper, P.Y. Zavalij, and M.P. Doyle Org. Lett. 14 2012 1676
54. D.M. Jaber, R.N. Burgin, M. Hepler, P. Zavalij, and M.P. Doyle Chem. Commun. 2011 7623
55. S. Kitagaki, Y. Yanamoto, H. Tsutsui, M. Anada, M. Nakajima, and S. Hashimoto Tetrahedron Lett. 42 2001 6361
56. J.S. Clark, and G.A. Whitlock Tetrahedron Lett. 35 1994 6381
57. J.S. Clark, F. Labre, and L.H. Thomas Org. Biomol. Chem. 9 2011 4823
58. J.S. Clark, T.C. Fessard, and C. Wilson Org. Lett. 6 2004 1773
59. M.P. Doyle, K. Kundu, and A.E. Russell Org. Lett. 7 2005 5171
60. J.S. Clark, A.L. Bate, and T. Grinter Chem. Commun. 2001 459
61. J.S. Clark, C. Guerot, C. Wilson, and A.J. Blake Chem. Commun. 2007 4134
62. J.S. Clark, S.B. Walls, C. Wilson, S.P. East, and M.J. Drysdale Eur. J. Org. Chem. 2 2006 323
63. A. Padwa, J.M. Kassir, M.A. Semones, and M.D. Weingarten J. Org. Chem. 60 1995 53
64. D.M. Hodgson, D. Angrish, S.P. Erickson, J. Kloesges, and C.H. Lee Org. Lett. 10 2008 5553
65. D.M. Hodgson, and S. Man Chem. - Eur. J. 17 2011 9731
66. A.R. Thornton, and S.B. Blakey J. Am. Chem. Soc. 130 2008 5020
67. T. Yakura, W. Muramatsu, and J. Uenishi Chem. Pharm. Bull. 53 2005 989
68. M.P. Doyle, M.N. Protopopova, C.D. Poulter, and D.H. Rogers J. Am. Chem. Soc. 117 1995 7281
69. M.P. Doyle, and W.H. Hu Synlett 2001 1364
70. M.P. Doyle, and W.H. Hu J. Org. Chem. 65 2000 8839
71. T.M. Weathers, Y.H. Wang, and M.P. Doyle J. Org. Chem. 71 2006 8183
72. N.P. Karche, S.M. Jachak, and D.D. Dhavale J. Org. Chem. 68 2003 4531
73. G.K. Murphy, and F.G. West Org. Lett. 8 2006 4359
74. H.T. Bonge, and T. Hansen Tetrahedron Lett. 49 2008 57
75. L. Thijs, and B. Zwanenburg Tetrahedron 36 1980 2145
76. J.S. Clark, A.G. Dossetter, and W.G. Whittingham Tetrahedron Lett. 37 1996 5605
77. J.S. Clark, and Y.S. Wong Chem. Commun. 2000 1079
78. R.W. Tester, and F.G. West Tetrahedron Lett. 39 1998 4631
79. F.P. Marmsater, G.K. Murphy, and F.G. West J. Am. Chem. Soc. 125 2003 14724
80. M.A. Calter, and P.M. Sugathapala Tetrahedron Lett. 39 1998 8813
81. N. Shimada, S. Nakamura, M. Anada, M. Shiro, and S. Hashimoto Chem. Lett. 38 2009 488
82. C.D. Gutsche, and M. Hillman J. Am. Chem. Soc. 76 1954 2236
83. J.B. Brogan, C.B. Bauer, R.D. Rogers, and C.K. Zercher Tetrahedron Lett. 37 1996 5053
84. J.B. Brogan, C.K. Zercher, C.B. Bauer, and R.D. Rogers J. Org. Chem. 62 1997 3902
85. A. Oku, N. Murai, and J. Baird J. Org. Chem. 62 1997 2123
86. A. Oku, S. Ohki, T. Yoshida, and K. Kimura Chem. Commun. 1996 1077
87. A. Oku, Y. Sawada, M. Schroeder, I. Higashikubo, T. Yoshida, and S. Ohki J. Org. Chem. 69 2004 1331
88. T. Kamada, Geqing, M. Abe, and A. Oku J. Chem. Soc., Perkin Trans. 1 1996 413
89. A. Oku, and M. Numata J. Org. Chem. 65 2000 1899
90. T. Mori, and A. Oku Chem. Commun. 1999 1339
91. Y. Sawada, T. Mori, and A. Oku Chem. Commun. 2001 1086
92. Y. Sawada, T. Mori, and A. Oku J. Org. Chem. 68 2003 10040
93. S. Muthusamy, J. Krishnamurthi, and E. Suresh Chem. Commun. 2007 861
94. J.S. Clark, S.T. Hayes, C. Wilson, and L. Gobbi Angew. Chem., Int. Ed. 46 2007 437
95. J.S. Clark, R. Berger, S.T. Hayes, L.H. Thomas, A.J. Morrison, and L. Gobbi Angew. Chem., Int. Ed. 49 2010 9867
96. J.S. Clark, A.G. Dossetter, A.J. Blake, W.S. Li, and W.G. Whittingham Chem. Commun. 1999 749
97. J.S. Clark, C.A. Baxter, A.G. Dossetter, S. Poigny, J.L. Castro, and W.G. Whittingham J. Org. Chem. 73 2008 1040
98. J.S. Clark, C.A. Baxter, and J.L. Castro Synthesis-Stuttgart 19 2005 3398
99. J.S. Clark, D. Vignard, and A. Parkin Org. Lett. 13 2011 3980
100. J.B. Brogan, and C.K. Zercher Tetrahedron Lett. 39 1998 1691
101. C. Stewart, R. McDonald, and F.G. West Org. Lett. 13 2011 720