Mitsunobu Reaction of Unbiased Cyclic Allylic Alcohols

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8294-8303

  Shull, Brian K ^a,b   Sakai, Takashi ^a,c   Nichols, Jeffrey B ^a   Koreeda, Masato ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b Glycosyn Inc   (United States)

^c OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000824652     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9615155     Document Type: Article

References (121)

1. Cooper, E. L.; Yankee, E. W. J. Am. Chem. Soc. 1975, 96, 5876.
2. (b) Corey, E. J.; Nicolaou, K. C.; Shibasaki, M.; Machida, Y.; Shiner, C. S. Tetrahedron Lett. 1975, 3183.
3. (c) Vorbruggen, H. Justus Leibigs Ann. Chem. 1974, 821.
4. (d) Floyd, D. M.; Crosby, G.; Weinshenker A. Tetrahedron Lett. 1972, 3265, 3269.
5. (e) Latrell, R.; Lohaus, G. Justus Liebigs Ann. Chem. 1974, 901.
6. (f) Raduchel, B. Synthesis 1980, 292.
7. (g) Kruizinga, W. H.; Strijtveen, B.; Kellog, R. M. J. Org. Chem. 1981, 46, 4321.
8. (h) Huffman, J. W.; Desai, R. C. Synth. Commun. 1983, 13, 553.
9. (i) Crossland, R. K.; Servis, K. L. J. Org. Chem. 1970, 35, 3195.
10. (j) Mukaiyama, T.; Hojo, K. Chem. Lett. 1976, 893.
11. (k) Sato, T.; Otera, J. Synlett 1995, 336.
12. (l) Castro, J. L.; Matassa, V. G. J. Org. Chem. 1994, 59, 2289.
13. (m) Boivin, J.; Henriet, E.; Zard, S. Z. J. Am. Chem. Soc. 1994, 116, 9739.
14. (n) Moriarty, R. M.; Zhuang, H.; Penmasta, R.; Liu, K.; Awasthi, A. K.; Tuladhar, S. M.; Rao, M. S. C.; Singh, V. K. Tetrahedron Lett. 1993, 34, 8029.
15. (a) Mitsunobu, O.; Masahiko, E. Bull. Chem. Soc. Jpn. 1971, 44, 3427.
16. (b) Mitsunobu, O.; Wada, M.; Sano, T. J. Am. Chem. Soc. 1972, 94, 679.
17. (c) Wada, M.; Sano, T.; Mitsunobu, O. Bull. Chem. Soc. Jpn. 1973, 46, 2833.
18. (d) Morimoto, H.; Furukawa, T.; Miyazima, K.; Mitsunobu, O. Chem. Lett. 1973, 821.
19. Reviews: (e) Mitsunobu, O. Synthesis 1981, 1. (f) Hughes, D. L. Organic Reactions; John Wiley & Sons: New York, 1972; Vol. 42, Chapter 2, pp 335-656. (g) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127.
20. Reviews: (e) Mitsunobu, O. Synthesis 1981, 1. (f) Hughes, D. L. Organic Reactions; John Wiley & Sons: New York, 1972; Vol. 42, Chapter 2, pp 335-656. (g) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127.
21. Reviews: (e) Mitsunobu, O. Synthesis 1981, 1. (f) Hughes, D. L. Organic Reactions; John Wiley & Sons: New York, 1972; Vol. 42, Chapter 2, pp 335-656. (g) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127.
22. (a) Camp, D.; Hanson, G. R.; Jenkins, I. D. J. Org. Chem. 1995, 60, 2977.
23. (b) Crich, D.; Yao, Q.; Filzen, F. J. Am. Chem. Soc. 1995, 117, 11455.
24. Crich, D.; Dyker, H.; Harris, R. J. J. Org. Chem. 1989, 54, 257.
25. (a) Morrison, D. C. J. Org. Chem. 1958, 23, 1072.
26. (b) Brunn, E.; Huisgen, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 513.
27. (a) Guthrie, R. D.; Jenkins, I. D. Aust. J. Chem. 1982, 35, 767.
28. (b) Von Itzstein, M.; Jenkins, I. D. Aust. J. Chem. 1983, 36, 557;
29. (c) 1984, 37, 2447.
30. (d) Von Itzstein, M.; Jenkins, I. D. J. Chem. Soc., Perkin Trans. 1 1986, 437;
31. (e) 1987, 2057.
32. (f) Grochowski, E.; Hilton, B. D.; Kupper, R. J.; Michejda, C. J. J. Am. Chem. Soc. 1982, 104, 6876.
33. (a) Varasi, M.; Walker, K. A. M.; Maddox, M. L. J. Org. Chem. 1987, 52, 4235.
34. (b) Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487.
35. (a) Camp, D.; Jenkins, I. D. J. Org. Chem. 1989, 54, 3045, 3049.
36. (a) Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017.
37. (b) Koppel, I.; Koppel, J.; Degerbeck, F.; Grehn, L.; Ragnarsson, U. J. Org. Chem. 1991, 56, 7172.
38. (c) Saïsh, M.; Besspdes, M.; Antonakis, K. Tetrahedron Lett. 1992, 33, 4317.
39. (d) Koppel, I.; Koppel, J.; Koppel, I.; Leito, I.; Pihl, V.; Wallin, A.; Grehn, L.; Ragnarsson, U. J. Chem. Soc., Perkin Trans. 2 1993, 655.
40. (e) Warmerdam, E. G. J. C.; Brussee, J.; Kruse, C. G.; van der Gen, A. Tetrahedron 1993, 49, 1063.
41. (f) Dodge, J. A.; Trujillo, J. I.; Presnell, M. J. Org. Chem. 1994, 59, 234.
42. (g) Hughes, D. L.; Reamer, R. A. J. Org. Chem. 1996, 61, 2967.
43. (a) Pautard, A. M.; Evans, S. A. J. Org. Chem. 1988, 53, 2300.
44. (b) Pautard-Cooper, A.; Evans, S. A. J. Org. Chem. 1989, 54, 2485.
45. For examples of very similar systems with significantly different results, see: (a) Dyong, I.; Weigand, J.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 577. (b) Dyong, I.; Merten, H.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 600. (c) Schulte, G.; Meyer, W.; Starkloff, A.; Dyong, I. Chem. Ber. 1981, 114, 1809. (d) Gauchet, F.; Julia, M.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1987, 1036. (e) Fiaud, J. C.; Aribi-Zouioueche, L. Tetrahedron Lett. 1982, 23, 5279. (f) Whitesell, J. K.; Fisher, M.; Jardine, P. D. S. J. Org. Chem. 1983, 48, 1556 and the results of ref 15 and this study, (g) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. (h) Pingli, L.; Vandewalle, M. Tetrahedron 1994, 50, 7061. (i) Mereyala, H. B.; Gaddam, B. R. J. Chem Soc., Perkin Trans. 1 1994, 2187.
46. For examples of very similar systems with significantly different results, see: (a) Dyong, I.; Weigand, J.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 577. (b) Dyong, I.; Merten, H.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 600. (c) Schulte, G.; Meyer, W.; Starkloff, A.; Dyong, I. Chem. Ber. 1981, 114, 1809. (d) Gauchet, F.; Julia, M.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1987, 1036. (e) Fiaud, J. C.; Aribi-Zouioueche, L. Tetrahedron Lett. 1982, 23, 5279. (f) Whitesell, J. K.; Fisher, M.; Jardine, P. D. S. J. Org. Chem. 1983, 48, 1556 and the results of ref 15 and this study, (g) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. (h) Pingli, L.; Vandewalle, M. Tetrahedron 1994, 50, 7061. (i) Mereyala, H. B.; Gaddam, B. R. J. Chem Soc., Perkin Trans. 1 1994, 2187.
47. For examples of very similar systems with significantly different results, see: (a) Dyong, I.; Weigand, J.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 577. (b) Dyong, I.; Merten, H.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 600. (c) Schulte, G.; Meyer, W.; Starkloff, A.; Dyong, I. Chem. Ber. 1981, 114, 1809. (d) Gauchet, F.; Julia, M.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1987, 1036. (e) Fiaud, J. C.; Aribi-Zouioueche, L. Tetrahedron Lett. 1982, 23, 5279. (f) Whitesell, J. K.; Fisher, M.; Jardine, P. D. S. J. Org. Chem. 1983, 48, 1556 and the results of ref 15 and this study, (g) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. (h) Pingli, L.; Vandewalle, M. Tetrahedron 1994, 50, 7061. (i) Mereyala, H. B.; Gaddam, B. R. J. Chem Soc., Perkin Trans. 1 1994, 2187.
48. For examples of very similar systems with significantly different results, see: (a) Dyong, I.; Weigand, J.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 577. (b) Dyong, I.; Merten, H.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 600. (c) Schulte, G.; Meyer, W.; Starkloff, A.; Dyong, I. Chem. Ber. 1981, 114, 1809. (d) Gauchet, F.; Julia, M.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1987, 1036. (e) Fiaud, J. C.; Aribi-Zouioueche, L. Tetrahedron Lett. 1982, 23, 5279. (f) Whitesell, J. K.; Fisher, M.; Jardine, P. D. S. J. Org. Chem. 1983, 48, 1556 and the results of ref 15 and this study, (g) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. (h) Pingli, L.; Vandewalle, M. Tetrahedron 1994, 50, 7061. (i) Mereyala, H. B.; Gaddam, B. R. J. Chem Soc., Perkin Trans. 1 1994, 2187.
49. For examples of very similar systems with significantly different results, see: (a) Dyong, I.; Weigand, J.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 577. (b) Dyong, I.; Merten, H.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 600. (c) Schulte, G.; Meyer, W.; Starkloff, A.; Dyong, I. Chem. Ber. 1981, 114, 1809. (d) Gauchet, F.; Julia, M.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1987, 1036. (e) Fiaud, J. C.; Aribi-Zouioueche, L. Tetrahedron Lett. 1982, 23, 5279. (f) Whitesell, J. K.; Fisher, M.; Jardine, P. D. S. J. Org. Chem. 1983, 48, 1556 and the results of ref 15 and this study, (g) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. (h) Pingli, L.; Vandewalle, M. Tetrahedron 1994, 50, 7061. (i) Mereyala, H. B.; Gaddam, B. R. J. Chem Soc., Perkin Trans. 1 1994, 2187.
50. For examples of very similar systems with significantly different results, see: (a) Dyong, I.; Weigand, J.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 577. (b) Dyong, I.; Merten, H.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 600. (c) Schulte, G.; Meyer, W.; Starkloff, A.; Dyong, I. Chem. Ber. 1981, 114, 1809. (d) Gauchet, F.; Julia, M.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1987, 1036. (e) Fiaud, J. C.; Aribi-Zouioueche, L. Tetrahedron Lett. 1982, 23, 5279. (f) Whitesell, J. K.; Fisher, M.; Jardine, P. D. S. J. Org. Chem. 1983, 48, 1556 and the results of ref 15 and this study, (g) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. (h) Pingli, L.; Vandewalle, M. Tetrahedron 1994, 50, 7061. (i) Mereyala, H. B.; Gaddam, B. R. J. Chem Soc., Perkin Trans. 1 1994, 2187.
51. For examples of very similar systems with significantly different results, see: (a) Dyong, I.; Weigand, J.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 577. (b) Dyong, I.; Merten, H.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 600. (c) Schulte, G.; Meyer, W.; Starkloff, A.; Dyong, I. Chem. Ber. 1981, 114, 1809. (d) Gauchet, F.; Julia, M.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1987, 1036. (e) Fiaud, J. C.; Aribi-Zouioueche, L. Tetrahedron Lett. 1982, 23, 5279. (f) Whitesell, J. K.; Fisher, M.; Jardine, P. D. S. J. Org. Chem. 1983, 48, 1556 and the results of ref 15 and this study, (g) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. (h) Pingli, L.; Vandewalle, M. Tetrahedron 1994, 50, 7061. (i) Mereyala, H. B.; Gaddam, B. R. J. Chem Soc., Perkin Trans. 1 1994, 2187.
52. For examples of very similar systems with significantly different results, see: (a) Dyong, I.; Weigand, J.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 577. (b) Dyong, I.; Merten, H.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 600. (c) Schulte, G.; Meyer, W.; Starkloff, A.; Dyong, I. Chem. Ber. 1981, 114, 1809. (d) Gauchet, F.; Julia, M.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1987, 1036. (e) Fiaud, J. C.; Aribi-Zouioueche, L. Tetrahedron Lett. 1982, 23, 5279. (f) Whitesell, J. K.; Fisher, M.; Jardine, P. D. S. J. Org. Chem. 1983, 48, 1556 and the results of ref 15 and this study, (g) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. (h) Pingli, L.; Vandewalle, M. Tetrahedron 1994, 50, 7061. (i) Mereyala, H. B.; Gaddam, B. R. J. Chem Soc., Perkin Trans. 1 1994, 2187.
53. For examples of very similar systems with significantly different results, see: (a) Dyong, I.; Weigand, J.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 577. (b) Dyong, I.; Merten, H.; Thiem, J. Justus Liebigs Ann. Chem. 1986, 600. (c) Schulte, G.; Meyer, W.; Starkloff, A.; Dyong, I. Chem. Ber. 1981, 114, 1809. (d) Gauchet, F.; Julia, M.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1987, 1036. (e) Fiaud, J. C.; Aribi-Zouioueche, L. Tetrahedron Lett. 1982, 23, 5279. (f) Whitesell, J. K.; Fisher, M.; Jardine, P. D. S. J. Org. Chem. 1983, 48, 1556 and the results of ref 15 and this study, (g) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. (h) Pingli, L.; Vandewalle, M. Tetrahedron 1994, 50, 7061. (i) Mereyala, H. B.; Gaddam, B. R. J. Chem Soc., Perkin Trans. 1 1994, 2187.
54. For some representative examples, see: (a) Danishefsky, S.; Berman, E. M.; Ciufolini, M.; Etheredge, A. J.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 3891. (b) Rao, A. V. R.; Yadav, J. S.; Reddy, K. B.; Mehendale, A. R. J. Chem. Soc., Chem. Commun. 1984, 453.
55. For some representative examples, see: (a) Danishefsky, S.; Berman, E. M.; Ciufolini, M.; Etheredge, A. J.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 3891. (b) Rao, A. V. R.; Yadav, J. S.; Reddy, K. B.; Mehendale, A. R. J. Chem. Soc., Chem. Commun. 1984, 453.
56. (a) Rao, A. V. R.; Yadav, J. S.; Reddy, K. B.; Mehendale, A. R. J. Chem. Soc., Chem. Commun. 1984, 453;
57. (b) Tetrahedron 1984, 40, 4643.
58. (c) Guindon, Y.; Delorme, D. Can. J. Chem. 1987, 65, 1438.
59. (d) Guindon, Y.; Delorme, D.; Lau, C. K.; Zamboni, R. J. Org. Chem. 1988, 53, 267.
60. Grynkiewicz, G.; Burzynska, H. Tetrahedron 1976, 32, 2109.
61. (a) Trost, B. M.; Edstrom, E. D. Angew. Chem., Int. Ed. Engl. 1990, 29, 520.
62. (b) Castedo, L.; Mascarenas, J. L.; Mourino, A. Tetrahedron Lett. 1987, 28, 2099.
63. (c) Johnson, B. M.; Vollhardt, K. P. C. Synlett 1990, 209.
64. (d) Fleming, I.; Higgins, D.; Lawrence, N. J.; Thomas, A. P. J. Chem. Soc., Perkin Trans. 1 1992, 3331.
65. (e) Carda, M.; Marco, J. A. Tetrahedron 1992, 48, 9789.
66. (f) Suemune, H.; Matsuno, K.; Uchida, M.; Sakai, K. Tetrahedron: Asymmetry 1992, 3, 297.
67. (g) Balan, A.; Ziffer, H. J. Chem. Soc., Chem. Commun. 1990, 175 and ref 30.
68. Farina, V. Tetrahedron Lett. 1989, 30, 6645.
69. Luche, J.; Gemal, A. L. J. Am. Chem. Soc. 1981, 103, 5454.
70. The only exceptions found: (a) Danda, H.; Nagatomi, T.; Maehara, A.; Umemura, T. Tetrahedron 1991, 47, 8701. (b) Takano, S.; Suzuki, M.; Ogasawara, K. Tetrahedron: Assymmetry 1993, 4, 1043. (c) Wachtmeister, J.; Classon, B.; Samuelsson, B. Tetrahedron 1995, 57, 2029 and ref 15.
71. The only exceptions found: (a) Danda, H.; Nagatomi, T.; Maehara, A.; Umemura, T. Tetrahedron 1991, 47, 8701. (b) Takano, S.; Suzuki, M.; Ogasawara, K. Tetrahedron: Assymmetry 1993, 4, 1043. (c) Wachtmeister, J.; Classon, B.; Samuelsson, B. Tetrahedron 1995, 57, 2029 and ref 15.
72. The only exceptions found: (a) Danda, H.; Nagatomi, T.; Maehara, A.; Umemura, T. Tetrahedron 1991, 47, 8701. (b) Takano, S.; Suzuki, M.; Ogasawara, K. Tetrahedron: Assymmetry 1993, 4, 1043. (c) Wachtmeister, J.; Classon, B.; Samuelsson, B. Tetrahedron 1995, 57, 2029 and ref 15.
73. (a) Kantner, S. S.; Humski, K.; Georing, H. L. J. Am. Chem. Soc. 1982, 104, 1693.
74. (b) Georing, H. L.; Paisley, S. D.; J. Org. Chem. 1987, 52, 943.
75. Kawasaki, M.; Suzuki, Y.; Terashima, S. Chem. Pharm. Bull. 1985, 33, 52.
76. (a) Senda, Y.; Imaizumi, S. Tetrahedron 1974, 30, 3813.
77. (b) Lessard, J.; Tan, P. V. N.; Martino, R.; Saunders, J. K. Can. J. Chem. 1977, 55, 1015.
78. (c) Ouedraogo, A.; Viet, M. T. P.; Saunders, J. K.; Lessard, J. Can. J. Chem. 1987, 65, 1761.
79. The A value is not expected to be much greater than that of a methoxy group. For A values of similar substituants, see: Eliel, E. L.; Wilen, S. L. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; pp 690-700 (cyclohexanes) and pp 726-730 (cyclohexenes) and references cited within.
80. N2′ syn addition over anti addition, see (d) Magid, R. M. Tetrahedron 1980, 36, 1901.
81. N2′ syn addition over anti addition, see (d) Magid, R. M. Tetrahedron 1980, 36, 1901.
82. N2′ syn addition over anti addition, see (d) Magid, R. M. Tetrahedron 1980, 36, 1901.
83. N2′ syn addition over anti addition, see (d) Magid, R. M. Tetrahedron 1980, 36, 1901.
84. (a) Gallina, C.; Ciattini, P. G. J. Am. Chem. Soc. 1979, 101, 1035.
85. (b) Goering, H. L.; Kantner, S. S. J. Org. Chem. 1981, 46, 2144,
86. (c) Gallina, C. Tetrahedron Lett. 1982, 23, 3093.
87. (d) Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715.
88. (e) Goering, H. L.; Tseng, C. C. J. Org. Chem. 1985, 50, 1597.
89. (f) Fleming, I.; Thomas, A. P. J. Chem. Soc., Chem. Commun. 1986, 1456.
90. (g) Underiner, T. L.; Goering, H. L. J. Org. Chem. 1989, 54, 3239.
91. N2′ reactions are in favor of anti attack: (h) Wipf, P.; Fritch, P. C. J. Org. Chem. 1994, 59, 4875. (i) Marshal, J. A. Chem Rev. 1989, 89, 1503. (j) Corey, E. J.; Boaz, N. W. Tetrahedron 1984, 25, 3063. (k) Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984.
92. N2′ reactions are in favor of anti attack: (h) Wipf, P.; Fritch, P. C. J. Org. Chem. 1994, 59, 4875. (i) Marshal, J. A. Chem Rev. 1989, 89, 1503. (j) Corey, E. J.; Boaz, N. W. Tetrahedron 1984, 25, 3063. (k) Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984.
93. N2′ reactions are in favor of anti attack: (h) Wipf, P.; Fritch, P. C. J. Org. Chem. 1994, 59, 4875. (i) Marshal, J. A. Chem Rev. 1989, 89, 1503. (j) Corey, E. J.; Boaz, N. W. Tetrahedron 1984, 25, 3063. (k) Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984.
94. N2′ reactions are in favor of anti attack: (h) Wipf, P.; Fritch, P. C. J. Org. Chem. 1994, 59, 4875. (i) Marshal, J. A. Chem Rev. 1989, 89, 1503. (j) Corey, E. J.; Boaz, N. W. Tetrahedron 1984, 25, 3063. (k) Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984.
95. See ref 17.
96. Wharton, P. S.; Bohlen, D. H. J. Org. Chem. 1961, 26, 3615.
97. (a) Dominianni, S. J.; Ryan, C. W.; DeArmitt, C. W. J. Org. Chem. 1977, 42, 344.
98. (b) Sardina, F. J.; Johnston, A. D.; Mourino, A.; Okamura, W. J. Org. Chem. 1982, 47, 1576.
99. Reference deleted.
100. (a) Grandi, R.; Pagnori, U. M.; Trave, R.; Granti, L. Tetrahedron 1974, 30, 4037.
101. For the intermediates, see: (b) Birch, A. J.; Walker, K. A. M. J. Chem. Soc. C 1966, 1894. (c) Klein, E.; Ohloff, G. Tetrahedron 1963, 1091. (d) Tadwalker, V. R.; Narayanaswamy, M.; Rao, A. S. Indian J. Chem. 1971, 1223. (e) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
102. For the intermediates, see: (b) Birch, A. J.; Walker, K. A. M. J. Chem. Soc. C 1966, 1894. (c) Klein, E.; Ohloff, G. Tetrahedron 1963, 1091. (d) Tadwalker, V. R.; Narayanaswamy, M.; Rao, A. S. Indian J. Chem. 1971, 1223. (e) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
103. For the intermediates, see: (b) Birch, A. J.; Walker, K. A. M. J. Chem. Soc. C 1966, 1894. (c) Klein, E.; Ohloff, G. Tetrahedron 1963, 1091. (d) Tadwalker, V. R.; Narayanaswamy, M.; Rao, A. S. Indian J. Chem. 1971, 1223. (e) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
104. For the intermediates, see: (b) Birch, A. J.; Walker, K. A. M. J. Chem. Soc. C 1966, 1894. (c) Klein, E.; Ohloff, G. Tetrahedron 1963, 1091. (d) Tadwalker, V. R.; Narayanaswamy, M.; Rao, A. S. Indian J. Chem. 1971, 1223. (e) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
105. (a) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1992, 443.
106. (b) Mori, M.; Saitoh, F.; Uesaka, N.; Shibasaki, M. Chem. Lett. 1993, 213.
107. (c) Uesaka, N.; Saitoh, F.; Mori, M.; Shibasaki, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 5633.
108. (a) Epiotis, N. D.; Cherry, W. R.; Shaik, S.; Yates, R. L.; Bernardi, F. Top. Curr. Chem. 1977, 70, 1. See also ref 22c.
109. Still, W. C.; Kahn, M.; Mitra, A. J. J. Org. Chem. 1978, 43, 2923.
110. See ref 19.
111. (a) Cain, D.; Procter, K.; Cassel, R. A. J. Org. Chem. 1984, 49, 2647.
112. (b) Choudary, B. M.; Prasad, A. D.; Swapna, V.; Valli, V. L. K.; Bhuma, V. Tetrahedron 1992, 48, 953.
113. (c) Gorthey, L. A.; Vairamani, M.; Djerassi, C. J. Org. Chem. 1985, 50, 4173.
114. (d) Bambridge, K.; Clark, B. P.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1995, 2535.
115. (a) Chamberlain, P.; Roberts, M. L.; Whitham, G. H. J. Chem. Soc. B 1970, 1374.
116. (b) Adam, W.; Smerz, A. Tetrahedron 1995, 51, 13039.
117. (a) Klein, E.; Ohloff, G. Tetrahedron 1963, 1091.
118. (b) Tadwalker, V. R.; Narayanaswamy, M.; Rao, A. S. Indian J. Chem. 1971, 1223 and references 29a,b.
119. (a) Read, J.; Swann, G. J. Chem. Soc. 1937, 239.
120. (b) Mills, J. A. J. Chem. Soc. 1952, 4976.
121. (c) Schroeter, S. H.; Eliel, E. L. J. Org. Chem. 1965, 30, 1.