Mechanism and applications of lithium amide-induced asymmetric rearrangements of 4-substituted and 4,4-disubstituted cyclopentene oxides to cyclopentenols

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 24, 1999, Pages 3579-3590

  Hodgson, David M ^a,b   Gibbs, Andrew R ^a,b   Drew, Michael G B ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000005898     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907522d     Document Type: Article

References (67)

1. J. K. Crandall and M. Apparu, Org. React. (N. Y.), 1983, 29, 345;
2. T. Satoh, Chem. Rev., 1996, 96, 3303.
3. P. J. Cox and N. S. Simpkins, Tetrahedron: Asymmetry, 1991, 2, 1;
4. M. Asami, J. Synth. Org. Chem. Jpn., 1996, 54, 188;
5. D. M. Hodgson, A. R. Gibbs and G. P. Lee, Tetrahedron, 1996, 52, 14361;
6. P. O'Brien, J. Chem. Soc., Perkin Trans. 1, 1998, 1439.
7. Preliminary communication: D. M. Hodgson and A. R. Gibbs, Tetrahedron Lett., 1997, 38, 8907.
8. Preliminary communication: D. M. Hodgson and A. R. Gibbs, Tetrahedron: Asymmetry, 1996, 7, 407.
9. Preliminary communication: D. M. Hodgson and A. R. Gibbs, Synlett, 1997, 657.
10. R. P. Thummel and B. Rickborn, J. Am. Chem. Soc., 1970, 92, 2064.
11. K. M. Morgan and J. J. Gajewski, J. Org. Chem., 1996, 61, 820.
12. D. Milne and P. J. Murphy, J. Chem. Soc., Chem. Commun., 1993, 884; corrigendum, 1994, 675.
13. D. M. Hodgson, J. Witherington and B. A. Moloney, J. Chem. Soc., Perkin Trans. 1, 1994, 3373.
14. M. Asami, Bull. Chem. Soc. Jpn., 1990, 63, 1402.
15. S. Torii, T. Inokuchi, R. Oi, K. Kondo and T. Kobayashi, J. Org. Chem., 1986, 51, 254.
16. Dr Murphy agrees with the revised assignment (personal communication).
17. J. S. Chickos, M. Bausch and R. Alul, J. Org. Chem., 1981, 46, 3559;
18. see also: J. S. Chickos, J. Y.-J. Uang and T. A. Keiderling, J. Org. Chem., 1991, 56, 2594.
19. J. M. Bobbitt, L. H. Amundsen and R. I. Steiner, J. Org. Chem., 1960, 25, 2230.
20. J.-P. Deprés and A. E. Greene, J. Org. Chem., 1984, 49, 928.
21. A. Hutchinson, M. Grim and J. Chen, J. Heterocycl. Chem., 1989, 26, 451.
22. A. R. Gibbs, D Phil Thesis, University of Oxford, 1998.
23. D. M. Hodgson, G. P. Lee, R. E. Marriott, A. J. Thompson, R. Wisedale and J. Witherington, J. Chem. Soc., Perkin Trans. 1, 1998, 2151.
24. G. R. Krow, Org. React. (N.Y.), 1993, 43, 251;
25. M. S. Cooper, H. Heaney, A. J. Newbold and W. R. Sanderson, Synlett, 1990, 533;
26. H.-J. Kang and H.-S. Jeong, Bull. Korean Chem. Soc., 1996, 17, 5.
27. I. Saito, R. Nagata, K. Yuba and T. Matsuura, Tetrahedron Lett., 1983, 24, 1737.
28. Spectral data for unlabelled 20/21: T. T. Curran, D. A. Hay, C. P. Koegel and J. C. Evans, Tetrahedron, 1997, 53, 1983.
29. K. Fuji, Chem. Rev., 1993, 93, 2037;
30. E. J. Corey and A. Guzman-Perez, Angew. Chem., Int. Ed., 1998, 37, 388.
31. H. Paulsen and U. Maaß, Chem. Ber., 1981, 114, 346;
32. J. A. Cipollina, E. H. Ruediger, J. S. New, M. E. Wire, T. A. Shepherd, D. W. Smith and J. P. Yevich, J. Med. Chem., 1991, 34, 3316.
33. K. Kato, H. Suzuki, H. Tanaka and T. Miyasaka, Tetrahedron: Asymmetry, 1998, 9, 911;
34. K. Kato, H. Suzuki, H. Tanaka, T. Miyasaka, M. Baba, K. Yamaguchi and H. Akita, Chem. Pharm. Bull., 1999, 47, 1256.
35. M. P. Arrington and A. I. Meyers, Chem. Commun., 1999, 1371.
36. S. Czernecki, K. Vijayakumaran and G. Ville, J. Org. Chem., 1986, 51, 5472.
37. E. A. Mash and J. A. Fryling, J. Org. Chem., 1987, 52, 3000.
38. E. J. Corey and X.-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1989, p. 249.
39. A. Fukuzawa, H. Sato and T. Masamune, Tetrahedron Lett., 1987, 28, 4303.
40. D. L. Hughes, Org. React., 1992, 42, 335.
41. S. Raucher and D. C. Schindele, Synth. Commun., 1987, 17, 637.
42. M. J. Begley, J. P. Madeley, G. Pattenden and G. F. Smith, J. Chem. Soc., Perkin Trans. 1, 1992, 57.
43. (a) E. J. Corey and P. A. Grieco, Tetrahedron Lett., 1972, 107;
44. (b) E. J. Corey and B. B. Snider, J. Org. Chem., 1974, 39, 256;
45. (c) P. A. Grieco, J. Inanaga, N.-H. Lin and T. Yanami, J. Am. Chem. Soc., 1982, 104, 5781.
46. E. J. Corey and T.-P. Loh, J. Am. Chem. Soc., 1991, 113, 8966.
47. P. A. Grieco and C. V. Srinivasan, J. Org. Chem., 1981, 46, 2591.
48. For a recent review of iridoid syntheses see: A. Nangia, G. Prasuna and P. B. Rao, Tetrahedron, 1997, 53, 14507.
49. For more recent approaches see: A. V. Stepanov and V. V. Veselovsky, Russ. Chem. Bull., 1997, 46, 1606;
50. T. Horikawa, Y. Norimine, M. Tanaka, K. Sakai and H. Suemune, Chem. Pharm. Bull., 1998, 46, 17.
51. D. P. Curran, M.-H. Chen, D. Leszczweski, R. L. Elliott and D. M. Rakiewicz, J. Org. Chem., 1986, 51, 1612.
52. G. W. K. Cavill, D. L. Ford and H. D. Locksley, Aust. J. Chem., 1956, 9, 288.
53. (a) A. Nangia and G. Prasuna, Tetrahedron, 1996, 52, 3435;
54. (b) A. Nangia and G. Prasuna and P. B. Rao, Tetrahedron Lett., 1994, 35, 3755.
55. Unlabelled 15: Y. Bahurel, F. Collonges, A. Menet, F. Pautet, A. Poncet and G. Descotes, Bull. Soc. Chim. Fr., 1971, 2203;
56. K. Griesbaum, P. Krieger-Beck and J. Beck, J. Org. Chem., 1991, 56, 4005.
57. Spectral data for unlabelled 17: S. E. Cremer and C. Blankenship, J. Org. Chem., 1982, 47, 1626.
58. Preparation and spectral data for unlabelled 18: F. David, J. Org. Chem., 1981, 46, 3512.
59. Spectral data for unlabelled 19: P. E. Eaton, R. S. Sidhu, G. E. Langford, D. A. Cullison and C. L. Pietruszewski, Tetrahedron, 1981, 37, 4479.
60. K. Shishido, K. Hiroya, K. Fukumoto and T. Kametani, J. Chem. Res., 1989, (S) 100; (M) 0867.
61. W. Kabsch, J. Appl. Crystallogr., 1988, 21, 916.
62. G. M. Sheldrick, SHELXS-86, Acta Crystallogr., Sect. A, 1990, 46, 467.
63. G. M. Sheldrick, SHELXL-93, 1993, University of Göttingen, Germany, 1993.
64. P. G. M. Wuts, Synth. Commun., 1981, 11, 139.
65. (a) T.-F. Wang and C.-F. Yang, J. Chem. Soc., Chem. Commun., 1993, 884;
66. (b) D. Friedrich and L. A. Paquette, J. Org. Chem., 1991, 56, 3831.
67. S. Brechbühler-Bader, C. J. Coscia, P. Loew, Ch. von Szczepanski and D. Arigoni, J. Chem. Soc., Chem. Commun., 1968, 136.