Prospects for stereocontrol in the reduction of aromatic compounds

Tetrahedron Asymmetry

Volumn 7, Issue 2, 1996, Pages 317-344

  Donohoe, Timothy J ^a   Garg, Rina ^a   Stevenson, Clare A ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; FURAN DERIVATIVE; PIPERIDINE DERIVATIVE; POLYCYCLIC HYDROCARBON; PYRROLIDINE DERIVATIVE; THIOPHENE DERIVATIVE;

CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; REVIEW; STEREOCHEMISTRY;

EID: 0030019967     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00001-8     Document Type: Review

References (130)

1. For general reviews of the Birch reduction see: (i) L. N. Mander in 'Comprehensive Organic Synthesis', B. M. Trost and I. Flamming (Ed), Pergamon, Volume 8, 1991; (ii) P. W. Rabideau and Z. Marcinow, Org. React., 1992, 42, 1; (iii) P. W. Rabideau, Tetrahedron, 1989, 45, 1579.
2. For general reviews of the Birch reduction see: (i) L. N. Mander in 'Comprehensive Organic Synthesis', B. M. Trost and I. Flamming (Ed), Pergamon, Volume 8, 1991; (ii) P. W. Rabideau and Z. Marcinow, Org. React., 1992, 42, 1; (iii) P. W. Rabideau, Tetrahedron, 1989, 45, 1579.
3. For general reviews of the Birch reduction see: (i) L. N. Mander in 'Comprehensive Organic Synthesis', B. M. Trost and I. Flamming (Ed), Pergamon, Volume 8, 1991; (ii) P. W. Rabideau and Z. Marcinow, Org. React., 1992, 42, 1; (iii) P. W. Rabideau, Tetrahedron, 1989, 45, 1579.
4. See ref 1(ii) page 9; C. Eaborn, R. A. Jackson and R. Pearce, J. Chem. Soc., Perkin Trans. 1, 1974, 2055.
5. F. Camps, J. Coll and J. Pascul, J. Org. Chem., 1967, 32, 2563.
6. H. O. House, R. C. Strickland and E. J. Zaiko, J. Org. Chem., 1976, 41, 2401.
7. A. G. Schultz, S. J. Kirinich and R. Rahm, Tetrahedron Lett., 1995, 36, 455.
8. J. L. Marshall and Ban-Huat Song, J. Org. Chem., 1975, 40, 1942; J. L. Marshall and L. Hall, Tetrahedron, 1981, 37, 1271.
9. J. L. Marshall and Ban-Huat Song, J. Org. Chem., 1975, 40, 1942; J. L. Marshall and L. Hall, Tetrahedron, 1981, 37, 1271.
10. E. Cotsaris and M. N. Paddon-Row, J. Chem. Soc.,Chem. Commun., 1982, 1206.
11. For example see, E. Fujita, M. Shibuya, S. Nakamura, Y. Okada and T. Fujita, J. Chem. Soc., Perkin Trans. 1, 1974, 165.
12. For a review see, A. G. Schultz, Acc. Chem. Res., 1990, 23, 207.
13. A. G. Schultz and P. Sundararaman, Tetrahedron Lett., 1984, 25, 4591; A. G. Schultz, P. J. McCloskey and P. Sundararaman, Tetrahedron Lett., 1985, 26, 1619; A. G. Schultz, P. Sundararaman, M. Macielag, F. P. Lavieri and M. Welch, Tetrahedron Lett., 1985, 26, 4575.
14. A. G. Schultz and P. Sundararaman, Tetrahedron Lett., 1984, 25, 4591; A. G. Schultz, P. J. McCloskey and P. Sundararaman, Tetrahedron Lett., 1985, 26, 1619; A. G. Schultz, P. Sundararaman, M. Macielag, F. P. Lavieri and M. Welch, Tetrahedron Lett., 1985, 26, 4575.
15. A. G. Schultz and P. Sundararaman, Tetrahedron Lett., 1984, 25, 4591; A. G. Schultz, P. J. McCloskey and P. Sundararaman, Tetrahedron Lett., 1985, 26, 1619; A. G. Schultz, P. Sundararaman, M. Macielag, F. P. Lavieri and M. Welch, Tetrahedron Lett., 1985, 26, 4575.
16. A. G. Schultz, M. Macielag, P. Sundararaman, A. G. Taveras and M. Welch, J. Am. Chem. Soc., 1988, 110, 7828.
17. P. J. McCloskey and A. G. Schultz, Heterocycles, 1987, 25, 437.
18. R. H. Crabtree and M. W. Davis, Organometallics, 1983, 2, 681.
19. A. G. Schultz, P. J. McCloskey and J. J. Court, J. Am. Chem. Soc., 1987, 109, 6493; A. G. Schultz, M. Macielag, D. E. Podhorez, J. C. Suhadolnik and R. K. Kullnig, J. Org. Chem., 1988, 53, 2456.
20. A. G. Schultz, P. J. McCloskey and J. J. Court, J. Am. Chem. Soc., 1987, 109, 6493; A. G. Schultz, M. Macielag, D. E. Podhorez, J. C. Suhadolnik and R. K. Kullnig, J. Org. Chem., 1988, 53, 2456.
21. P. J. McCloskey and A. G. Schultz, J. Org. Chem., 1988, 53, 1380.
22. For a general guide to stereoselective hydrogenation of a variety of aromatic substrates see, 'Stereochemistry of Heterogeneous Metal Catalysis', M. Bartók (Ed), Wiley, 1985.
23. 'Hydrogenation Methods,' P. N. Rylander, Academic, 1985; R. D. Schuetz and L. R. Caswell, J. Org. Chem., 1962, 27, 486
24. 'Hydrogenation Methods,' P. N. Rylander, Academic, 1985; R. D. Schuetz and L. R. Caswell, J. Org. Chem., 1962, 27, 486
25. R. P. Linstead, W. E. Doering, S. B. Davis, P. Levine and R. R. Whetstone, J. Am. Chem. Soc., 1942, 64, 1985.
26. R. D. Schuetz and L. R. Caswell, J. Org. Chem., 1962, 27, 486; S. Siegel, G. V. Smith, B. Dmuchovsky, D. Dubbell and W. Halpern, J. Am. Chem. Soc., 1962, 84, 3136.
27. R. D. Schuetz and L. R. Caswell, J. Org. Chem., 1962, 27, 486; S. Siegel, G. V. Smith, B. Dmuchovsky, D. Dubbell and W. Halpern, J. Am. Chem. Soc., 1962, 84, 3136.
28. S. N. Balasubrahmanyam and N. Balasubramanian, Tetrahedron, 1973, 29, 683.
29. F. Fache, S. Lehuede and M. Lemaire, Tetrahedron Lett., 1995, 36, 885.
30. P. Drognat-Landré, M. Lemaire, D. Richard and P. Gallezot, J. Mol. Cat., 1993, 78, 257; K. Nasar, F. Fache, M. Lemaire, J. C. Béziat, M. Besson and P. Gallezot, J. Mol. Cat., 1994, 87, 107.
31. P. Drognat-Landré, M. Lemaire, D. Richard and P. Gallezot, J. Mol. Cat., 1993, 78, 257; K. Nasar, F. Fache, M. Lemaire, J. C. Béziat, M. Besson and P. Gallezot, J. Mol. Cat., 1994, 87, 107.
32. P. W. Rabideau and E. G. Burkholder, J. Org. Chem., 1979, 44, 2354.
33. P. W. Rabideau and R. G. Harvey, Tetrahedron Lett., 1970, 4139; P. W. Rabideau and E. G. Burkholder, J. Org. Chem., 1978, 43, 4283.
34. P. W. Rabideau and R. G. Harvey, Tetrahedron Lett., 1970, 4139; P. W. Rabideau and E. G. Burkholder, J. Org. Chem., 1978, 43, 4283.
35. Z. Marcinow, D. K. Clawson and P. W. Rabideau, Tetrahedron, 1989, 45, 5441.
36. P. W. Rabideau, C. A. Husted and D. M. Young, J. Org. Chem., 1983, 48, 4149; P. W. Rabideau, L. M. Day, C. A. Husted, J. L. Mooney and D. M. Wetzel, J. Org. Chem., 1986, 51, 1681; Ref 1 (ii), P10.
37. P. W. Rabideau, C. A. Husted and D. M. Young, J. Org. Chem., 1983, 48, 4149; P. W. Rabideau, L. M. Day, C. A. Husted, J. L. Mooney and D. M. Wetzel, J. Org. Chem., 1986, 51, 1681; Ref 1 (ii), P10.
38. M. C. Grossel and R. C. Hayward, J. Chem. Soc., Perkin Trans. 2, 1976, 851.
39. H. O. House, R. C. Strickland and E. J. Zaiko, J. Org. Chem., 1976, 41, 2401.
40. R. G. Harvey and C. C. Davis, J. Org. Chem., 1969, 34, 3607; R. G. Harvey and L. Arzadon, Tetrahedron, 1969, 25, 4887; P. W. Rabideau, A. J. Maxwell and A. Sygula, J. Org. Chem., 1986, 51, 3181.
41. R. G. Harvey and C. C. Davis, J. Org. Chem., 1969, 34, 3607; R. G. Harvey and L. Arzadon, Tetrahedron, 1969, 25, 4887; P. W. Rabideau, A. J. Maxwell and A. Sygula, J. Org. Chem., 1986, 51, 3181.
42. R. G. Harvey and C. C. Davis, J. Org. Chem., 1969, 34, 3607; R. G. Harvey and L. Arzadon, Tetrahedron, 1969, 25, 4887; P. W. Rabideau, A. J. Maxwell and A. Sygula, J. Org. Chem., 1986, 51, 3181.
43. P. W. Rabideau and R. G. Harvey, J. Org. Chem., 1970, 35, 25.
44. P. W. Rabideau and Z. Marcinow, Tetrahedron Lett., 1988, 29, 3761.
45. S. Siegel in 'Comprehensive Organic Synthesis', B. M. Trost and I. Flemming (Ed), Pergamon, Volume 8, 1991; see ref 16, Page 276.
46. A. W. Weitkamp, Adv. Catal., 1968, 18, 41.
47. W. Strohmeier, W. Reholer-Stirnweiss and R. Fleishman, Z. Naturfursch., Teil B, 1970, 25, 1481; see also S. Siegel in 'Comprehensive Organic Synthesis', B. M. Trost and I. Flemming (Ed), Pergamon, Volume 8, 1991.
48. W. Strohmeier, W. Reholer-Stirnweiss and R. Fleishman, Z. Naturfursch., Teil B, 1970, 25, 1481; see also S. Siegel in 'Comprehensive Organic Synthesis', B. M. Trost and I. Flemming (Ed), Pergamon, Volume 8, 1991.
49. J. G. Berger, S. R. Teller, C. D. Adams and L. J. Guggenberger, Tetrahedron Lett., 1975, 1807; O. Repic and D. J. Long, Tetrahedron Lett., 1983, 24, 1115.
50. J. G. Berger, S. R. Teller, C. D. Adams and L. J. Guggenberger, Tetrahedron Lett., 1975, 1807; O. Repic and D. J. Long, Tetrahedron Lett., 1983, 24, 1115.
51. L. J. Dolby and G. W. Gribble, J. Heterocycl. Chem., 1966, 3, 124.
52. I. Butula and R. Kuhn, Angew. Int. Ed. Engl., 1968, 7, 208; S. A. Montie and R. R. Schmidt III, Tetrahedron, 1971, 27, 3331; Y. Nagai, A. Irie, Y. Masuda, M. Oka and H. Uno, J. Med. Chem., 1979, 22, 677.
53. I. Butula and R. Kuhn, Angew. Int. Ed. Engl., 1968, 7, 208; S. A. Montie and R. R. Schmidt III, Tetrahedron, 1971, 27, 3331; Y. Nagai, A. Irie, Y. Masuda, M. Oka and H. Uno, J. Med. Chem., 1979, 22, 677.
54. I. Butula and R. Kuhn, Angew. Int. Ed. Engl., 1968, 7, 208; S. A. Montie and R. R. Schmidt III, Tetrahedron, 1971, 27, 3331; Y. Nagai, A. Irie, Y. Masuda, M. Oka and H. Uno, J. Med. Chem., 1979, 22, 677.
55. For a general review see, G. W. Gribble in 'Comprehensive Organic Synthesis', B. M. Trost and I. Flemming (Ed), Pergamon, Volume 8,1991.
56. B. E. Maryanoff, D. F. McComsey and J. O. Nortey, J. Org. Chem., 1981, 46, 355; J. Berger, Synthesis, 1974, 508.
57. B. E. Maryanoff, D. F. McComsey and J. O. Nortey, J. Org. Chem., 1981, 46, 355; J. Berger, Synthesis, 1974, 508.
58. H. Kotsuki, Y. Ushio and M. Ochi, Heterocycles, 1987, 26, 1771.
59. See ref 35; B. E. Maryanoff and D. F. McComsey, J. Org. Chem., 1978, 43, 2733.
60. A. E. Lanzilotti, R. Littell, W. J. Fanshawe, T. C. McKenzie and F. M. Lovell, J. Org. Chem., 1979, 44, 4809.
61. J. G. Berger, F. Davidson and G. E. Langford, J. Med. Chem., 1977, 20, 600; A. J. Elliot and H. Guzik, Tetrahedron Lett., 1982, 23, 1983.
62. J. G. Berger, F. Davidson and G. E. Langford, J. Med. Chem., 1977, 20, 600; A. J. Elliot and H. Guzik, Tetrahedron Lett., 1982, 23, 1983.
63. G. W. Gribble, J. L. Johnson and M. G. Saulnier, Heterocycles, 1981, 16, 2109; J. G. Berger, P. Tahbaz, A. T. McPhail and K. D. Onan, Tetrahedron Lett., 1983, 24, 2469.
64. G. W. Gribble, J. L. Johnson and M. G. Saulnier, Heterocycles, 1981, 16, 2109; J. G. Berger, P. Tahbaz, A. T. McPhail and K. D. Onan, Tetrahedron Lett., 1983, 24, 2469.
65. A. J. Birch and J. Slobbe, Heterocycles, 1976, 5, 905; for a related reduction that utilises sodium cyanoborohydride as a reducing agent, see: D. M. Ketcha, K. P. Carpenter and Q. Zhou, J. Org. Chem., 1991, 56, 1318.
66. A. J. Birch and J. Slobbe, Heterocycles, 1976, 5, 905; for a related reduction that utilises sodium cyanoborohydride as a reducing agent, see: D. M. Ketcha, K. P. Carpenter and Q. Zhou, J. Org. Chem., 1991, 56, 1318.
67. G. G. Evans, J. Am. Chem. Soc., 1951, 73, 5230; D. M. Lemal, S. D. McGregor, J. Am. Chem. Soc., 1966, 88, 1335; C. B. Hudson and A. V. Robertson, Tetrahedron Lett., 1967, 4015.
68. G. G. Evans, J. Am. Chem. Soc., 1951, 73, 5230; D. M. Lemal, S. D. McGregor, J. Am. Chem. Soc., 1966, 88, 1335; C. B. Hudson and A. V. Robertson, Tetrahedron Lett., 1967, 4015.
69. G. G. Evans, J. Am. Chem. Soc., 1951, 73, 5230; D. M. Lemal, S. D. McGregor, J. Am. Chem. Soc., 1966, 88, 1335; C. B. Hudson and A. V. Robertson, Tetrahedron Lett., 1967, 4015.
70. See ref 46; S. Ohki and M. Yoshino, Chem. Pharm. Bull., 1968, 16, 269; C. G. Overberger, L. C. Palmer, B. S. Marks and N. R. Byrd, J. Am. Chem. Soc., 1955, 77, 4100; see also: T. Oishi, M. Hirama, L. R. Sita and S. Masamune, Synthesis, 1991, 789.
71. See ref 46; S. Ohki and M. Yoshino, Chem. Pharm. Bull., 1968, 16, 269; C. G. Overberger, L. C. Palmer, B. S. Marks and N. R. Byrd, J. Am. Chem. Soc., 1955, 77, 4100; see also: T. Oishi, M. Hirama, L. R. Sita and S. Masamune, Synthesis, 1991, 789.
72. See ref 46; S. Ohki and M. Yoshino, Chem. Pharm. Bull., 1968, 16, 269; C. G. Overberger, L. C. Palmer, B. S. Marks and N. R. Byrd, J. Am. Chem. Soc., 1955, 77, 4100; see also: T. Oishi, M. Hirama, L. R. Sita and S. Masamune, Synthesis, 1991, 789.
73. W. W. Turner, J. Heterocycl. Chem., 1986, 23, 327; H. A. Bates and H. Rapoport, J. Am. Chem. Soc., 1979, 101, 1259
74. W. W. Turner, J. Heterocycl. Chem., 1986, 23, 327; H. A. Bates and H. Rapoport, J. Am. Chem. Soc., 1979, 101, 1259
75. H. P. Kaiser and J. M. Muchowski, J. Org. Chem., 1984, 49, 4202.
76. H. Kato, E. Koshinaka, N. Ogawa, K. Yamagishi, K. Mitani, S. Kubo and M. Hanaoka, Chem. Pharm. Bull., 1980, 28, 2194; C. W. Jefford, T. Kubota and A. Zaslona, Helv. Chim. Acta., 1986, 69, 2048; C. W. Jefford, K. Sienkiewicz and S. R. Thornton, Helv. Chim. Acta., 1995, 78, 1511; T. J. Bond, R. Jenkins, A. C. Ridley and P. C. Taylor, J. Chem. Soc., Perkin Trans. 1, 1993, 2241; for (-)-167B see C. W. Jefford and Q. Tang and A. Zaslona, J. Am. Chem. Soc., 1991, 113, 3513; for monmorine see C. W. Jefford, Q. Tang and A. Zaslona, Helv. Chim. Acta, 1989, 72, 1749.
77. H. Kato, E. Koshinaka, N. Ogawa, K. Yamagishi, K. Mitani, S. Kubo and M. Hanaoka, Chem. Pharm. Bull., 1980, 28, 2194; C. W. Jefford, T. Kubota and A. Zaslona, Helv. Chim. Acta., 1986, 69, 2048; C. W. Jefford, K. Sienkiewicz and S. R. Thornton, Helv. Chim. Acta., 1995, 78, 1511; T. J. Bond, R. Jenkins, A. C. Ridley and P. C. Taylor, J. Chem. Soc., Perkin Trans. 1, 1993, 2241; for (-)-167B see C. W. Jefford and Q. Tang and A. Zaslona, J. Am. Chem. Soc., 1991, 113, 3513; for monmorine see C. W. Jefford, Q. Tang and A. Zaslona, Helv. Chim. Acta, 1989, 72, 1749.
78. H. Kato, E. Koshinaka, N. Ogawa, K. Yamagishi, K. Mitani, S. Kubo and M. Hanaoka, Chem. Pharm. Bull., 1980, 28, 2194; C. W. Jefford, T. Kubota and A. Zaslona, Helv. Chim. Acta., 1986, 69, 2048; C. W. Jefford, K. Sienkiewicz and S. R. Thornton, Helv. Chim. Acta., 1995, 78, 1511; T. J. Bond, R. Jenkins, A. C. Ridley and P. C. Taylor, J. Chem. Soc., Perkin Trans. 1, 1993, 2241; for (-)-167B see C. W. Jefford and Q. Tang and A. Zaslona, J. Am. Chem. Soc., 1991, 113, 3513; for monmorine see C. W. Jefford, Q. Tang and A. Zaslona, Helv. Chim. Acta, 1989, 72, 1749.
79. H. Kato, E. Koshinaka, N. Ogawa, K. Yamagishi, K. Mitani, S. Kubo and M. Hanaoka, Chem. Pharm. Bull., 1980, 28, 2194; C. W. Jefford, T. Kubota and A. Zaslona, Helv. Chim. Acta., 1986, 69, 2048; C. W. Jefford, K. Sienkiewicz and S. R. Thornton, Helv. Chim. Acta., 1995, 78, 1511; T. J. Bond, R. Jenkins, A. C. Ridley and P. C. Taylor, J. Chem. Soc., Perkin Trans. 1, 1993, 2241; for (-)-167B see C. W. Jefford and Q. Tang and A. Zaslona, J. Am. Chem. Soc., 1991, 113, 3513; for monmorine see C. W. Jefford, Q. Tang and A. Zaslona, Helv. Chim. Acta, 1989, 72, 1749.
80. H. Kato, E. Koshinaka, N. Ogawa, K. Yamagishi, K. Mitani, S. Kubo and M. Hanaoka, Chem. Pharm. Bull., 1980, 28, 2194; C. W. Jefford, T. Kubota and A. Zaslona, Helv. Chim. Acta., 1986, 69, 2048; C. W. Jefford, K. Sienkiewicz and S. R. Thornton, Helv. Chim. Acta., 1995, 78, 1511; T. J. Bond, R. Jenkins, A. C. Ridley and P. C. Taylor, J. Chem. Soc., Perkin Trans. 1, 1993, 2241; for (-)-167B see C. W. Jefford and Q. Tang and A. Zaslona, J. Am. Chem. Soc., 1991, 113, 3513; for monmorine see C. W. Jefford, Q. Tang and A. Zaslona, Helv. Chim. Acta, 1989, 72, 1749.
81. H. Kato, E. Koshinaka, N. Ogawa, K. Yamagishi, K. Mitani, S. Kubo and M. Hanaoka, Chem. Pharm. Bull., 1980, 28, 2194; C. W. Jefford, T. Kubota and A. Zaslona, Helv. Chim. Acta., 1986, 69, 2048; C. W. Jefford, K. Sienkiewicz and S. R. Thornton, Helv. Chim. Acta., 1995, 78, 1511; T. J. Bond, R. Jenkins, A. C. Ridley and P. C. Taylor, J. Chem. Soc., Perkin Trans. 1, 1993, 2241; for (-)-167B see C. W. Jefford and Q. Tang and A. Zaslona, J. Am. Chem. Soc., 1991, 113, 3513; for monmorine see C. W. Jefford, Q. Tang and A. Zaslona, Helv. Chim. Acta, 1989, 72, 1749.
82. S. R. Angle and J. P. Boyce, Tetrahedron Lett., 1995, 36, 6185.
83. T. Kinoshita and T. Miwa, J. Chem. Soc.,Chem. Commun., 1974, 181; T. Kinoshita, K. Miyano and T. Miwa, Bull. Chem. Soc. Jpn, 1975, 48, 1865; A. J. Birch and J. Slobbe, Tetrahedron Lett., 1976, 2079; H. R. Divanford and M. M. Joullié, Org. Prep. Proc. Int., 1977, 9, 94.
84. T. Kinoshita and T. Miwa, J. Chem. Soc.,Chem. Commun., 1974, 181; T. Kinoshita, K. Miyano and T. Miwa, Bull. Chem. Soc. Jpn, 1975, 48, 1865; A. J. Birch and J. Slobbe, Tetrahedron Lett., 1976, 2079; H. R. Divanford and M. M. Joullié, Org. Prep. Proc. Int., 1977, 9, 94.
85. T. Kinoshita and T. Miwa, J. Chem. Soc.,Chem. Commun., 1974, 181; T. Kinoshita, K. Miyano and T. Miwa, Bull. Chem. Soc. Jpn, 1975, 48, 1865; A. J. Birch and J. Slobbe, Tetrahedron Lett., 1976, 2079; H. R. Divanford and M. M. Joullié, Org. Prep. Proc. Int., 1977, 9, 94.
86. T. Kinoshita and T. Miwa, J. Chem. Soc.,Chem. Commun., 1974, 181; T. Kinoshita, K. Miyano and T. Miwa, Bull. Chem. Soc. Jpn, 1975, 48, 1865; A. J. Birch and J. Slobbe, Tetrahedron Lett., 1976, 2079; H. R. Divanford and M. M. Joullié, Org. Prep. Proc. Int., 1977, 9, 94.
87. T. Masamune, M. Ono and H. Matsue, Bull. Chem. Soc. Jpn, 1975, 48, 491.
88. J. E. Semple, P. C. Wang, Z. Lysenko and M. M. Joullié, J. Am. Chem. Soc., 1980, 102, 7505.
89. J. G. Smith and R. B. McCall, J. Org. Chem., 1980, 45, 3982.
90. See ref 16, Page 459; G. W. Gribble in 'Comprehensive Organic Synthesis', B. M. Trost and I. Flemming (Ed), Pergamon, Volume 8, 1991, P 603.
91. J. A. Moore and J. E. Kelly, Org. Prep. Proc. Int., 1972, 4, 289; J. A. Moore and J. E. Kelly, / Polym. Lett. Ed., 1975, 13, 333; J. E. Semple and M. M. Joullié, Hetereocycles, 1980, 14, 1825.
92. J. A. Moore and J. E. Kelly, Org. Prep. Proc. Int., 1972, 4, 289; J. A. Moore and J. E. Kelly, / Polym. Lett. Ed., 1975, 13, 333; J. E. Semple and M. M. Joullié, Hetereocycles, 1980, 14, 1825.
93. J. A. Moore and J. E. Kelly, Org. Prep. Proc. Int., 1972, 4, 289; J. A. Moore and J. E. Kelly, / Polym. Lett. Ed., 1975, 13, 333; J. E. Semple and M. M. Joullié, Hetereocycles, 1980, 14, 1825.
94. H. Gerlach and H. Wettler, Helv. Chim. Acta, 1974, 57, 2306; M. J. Arco, M. H. Trammell and J. D. White, J. Org. Chem., 1976, 41, 2075; U. Schmidt, J. Gombos, E. Hashinger and H. Zak, Chem. Ber., 1976, 109, 2628; U. Schmidt and J. Werner, J. Chem. Soc.,Chem. Commun., 1986, 996.
95. H. Gerlach and H. Wettler, Helv. Chim. Acta, 1974, 57, 2306; M. J. Arco, M. H. Trammell and J. D. White, J. Org. Chem., 1976, 41, 2075; U. Schmidt, J. Gombos, E. Hashinger and H. Zak, Chem. Ber., 1976, 109, 2628; U. Schmidt and J. Werner, J. Chem. Soc.,Chem. Commun., 1986, 996.
96. H. Gerlach and H. Wettler, Helv. Chim. Acta, 1974, 57, 2306; M. J. Arco, M. H. Trammell and J. D. White, J. Org. Chem., 1976, 41, 2075; U. Schmidt, J. Gombos, E. Hashinger and H. Zak, Chem. Ber., 1976, 109, 2628; U. Schmidt and J. Werner, J. Chem. Soc.,Chem. Commun., 1986, 996.
97. H. Gerlach and H. Wettler, Helv. Chim. Acta, 1974, 57, 2306; M. J. Arco, M. H. Trammell and J. D. White, J. Org. Chem., 1976, 41, 2075; U. Schmidt, J. Gombos, E. Hashinger and H. Zak, Chem. Ber., 1976, 109, 2628; U. Schmidt and J. Werner, J. Chem. Soc.,Chem. Commun., 1986, 996.
98. See G. W. Gribble in 'Comprehensive Organic Synthesis', B. M. Trost and I. Flemming (Ed), Pergamon, Volume 8, 1991.
99. W. G. Blenderman and M. M. Joullié, Synth. Commun., 1981, 11, 881; K. Nishiro, S. Yano, Y. Kohashi, K. Yamamoto and I. Murata, J. Am. Chem. Soc., 1979, 101, 5059.
100. W. G. Blenderman and M. M. Joullié, Synth. Commun., 1981, 11, 881; K. Nishiro, S. Yano, Y. Kohashi, K. Yamamoto and I. Murata, J. Am. Chem. Soc., 1979, 101, 5059.
101. P. N. Confalone, G. Pizzolato and M. R. Uskokovi'c, Helv. Chim. Acta, 1976, 59, 1005; P. N. Confalone, G. Pizzolato and M. R. Uskokovi'c, J. Org. Chem., 1977, 42, 135 .
102. P. N. Confalone, G. Pizzolato and M. R. Uskokovi'c, Helv. Chim. Acta, 1976, 59, 1005; P. N. Confalone, G. Pizzolato and M. R. Uskokovi'c, J. Org. Chem., 1977, 42, 135 .
103. D. N. Kursanov, Z. N. Parnes, G. I. Bolestova and L. I. Belen'kii, Tetrahedron, 1975, 31, 311; Z. N. Parnes, I. Yu, M. Lyakhovetsky, M. I. Kalinkir, D. N. Kursanov and L. I. Belen'kii, Tetrahedron, 1978, 34, 170 3.
104. D. N. Kursanov, Z. N. Parnes, G. I. Bolestova and L. I. Belen'kii, Tetrahedron, 1975, 31, 311; Z. N. Parnes, I. Yu, M. Lyakhovetsky, M. I. Kalinkir, D. N. Kursanov and L. I. Belen'kii, Tetrahedron, 1978, 34, 170 3.
105. See ref 59; S. I. Zav'yalov and O. V. Dorofeeva, Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 1634.
106. G. G. Ayerst and K. Schofield, J. Chem. Soc., 1958, 4097; Y. Sato, T. Iwashigo and T. Miyadera, Chem. Pharm. Bull., 1960, 8, 427; G. Lunn and E. B. Sansone, J. Org. Chem., 1986, 51, 513.
107. G. G. Ayerst and K. Schofield, J. Chem. Soc., 1958, 4097; Y. Sato, T. Iwashigo and T. Miyadera, Chem. Pharm. Bull., 1960, 8, 427; G. Lunn and E. B. Sansone, J. Org. Chem., 1986, 51, 513.
108. G. G. Ayerst and K. Schofield, J. Chem. Soc., 1958, 4097; Y. Sato, T. Iwashigo and T. Miyadera, Chem. Pharm. Bull., 1960, 8, 427; G. Lunn and E. B. Sansone, J. Org. Chem., 1986, 51, 513.
109. M. M. Cook and C. Djerassi, J. Am. Chem. Soc., 1973, 95, 3678; D. E. Caddy and J. H. P. Utley, J. Chem. Soc., Perkin Trans. 2, 1973, 1258; D. F. Barringer Jr, G. Berkelhammer, S. D. Carter, L. Goldman and A. E. Lanzilotti, J. Org. Chem., 1973, 38, 1933.
110. M. M. Cook and C. Djerassi, J. Am. Chem. Soc., 1973, 95, 3678; D. E. Caddy and J. H. P. Utley, J. Chem. Soc., Perkin Trans. 2, 1973, 1258; D. F. Barringer Jr, G. Berkelhammer, S. D. Carter, L. Goldman and A. E. Lanzilotti, J. Org. Chem., 1973, 38, 1933.
111. M. M. Cook and C. Djerassi, J. Am. Chem. Soc., 1973, 95, 3678; D. E. Caddy and J. H. P. Utley, J. Chem. Soc., Perkin Trans. 2, 1973, 1258; D. F. Barringer Jr, G. Berkelhammer, S. D. Carter, L. Goldman and A. E. Lanzilotti, J. Org. Chem., 1973, 38, 1933.
112. M. Tsuda and Y. Kawazoe, Chem. Pharm. Bull., 1970, 18, 2499.
113. G. A. Cooke and G. Fodor, Can. J. Chem., 1968, 46, 1105; G. Fodor, E. Bauerschmidt and J. Cymerman Craig, Can. J. Chem., 1969, 47, 4393.
114. G. A. Cooke and G. Fodor, Can. J. Chem., 1968, 46, 1105; G. Fodor, E. Bauerschmidt and J. Cymerman Craig, Can. J. Chem., 1969, 47, 4393.
115. Z. Horii, T. Imanishi, T. Tanaka, I. Mori, M. Hanaoka and C. Iwata, Chem. Pharm. Bull., 1972, 20, 1768.
116. P. S. Anderson and R. E. Lyle, Adv. Heterocycl. Chem., 1966, 6, 45; J. G. Keay, Adv. Heterocycl. Chem., 1986, 39, 1.
117. P. S. Anderson and R. E. Lyle, Adv. Heterocycl. Chem., 1966, 6, 45; J. G. Keay, Adv. Heterocycl. Chem., 1986, 39, 1.
118. J. Bosch, D. Mauleón, F. Boncompte and R. Granados, J. Heterocycl. Chem., 1981, 18, 263.
119. B. E. Blough and F. I. Carroll, Tetrahedron Lett., 1993, 34, 7239.
120. W. L. F. Armarego, J. Chem. Soc. (C), 1967, 377.
121. See reference 16, page 486.
122. F. W. Vierhapper and E. L. Eliel, J. Org. Chem., 1977, 42, 51; H. Booth and A. H. Bostock, J. Chem. Soc., Perkin Trans. 2, 1972, 615.
123. F. W. Vierhapper and E. L. Eliel, J. Org. Chem., 1977, 42, 51; H. Booth and A. H. Bostock, J. Chem. Soc., Perkin Trans. 2, 1972, 615.
124. T. Momose, S. Uchida, N. Yamaashi and T. Imanishi, Chem. Pharm. Bull., 1977, 25, 1436.
125. I. W. Mathison and W. L. Fowler Jr, J. Pharm. Sci., 1969, 58, 1238; I. W. Mathison and P. H Morgan, J. Org. Chem., 1974, 39, 3210.
126. I. W. Mathison and W. L. Fowler Jr, J. Pharm. Sci., 1969, 58, 1238; I. W. Mathison and P. H Morgan, J. Org. Chem., 1974, 39, 3210.
127. K. Sakanishi, M. Ohira, I. Mochida, H. Okazaki and I. Mochida, J. Chem. Soc., Perkin Trans. 2, 1988, 1769.
128. T. S. Balaban and A. T. Balaban, Tetrahedron Lett., 1987, 28, 1341.
129. A. G. Anastassiou and R. P. Cellura, J. Chem. Soc.,Chem. Commun., 1969, 1521.
130. T. Matsumoto, S. Imai, T. Yoshinori and K. Tsuruta, Bull. Chem. Soc. Jpn, 1987, 60, 2401.