Isomerisations of cycloalkene- and bicycloalkene-derived achiral epoxides by enantioselective α-deprotonation

Abstract

Enantioselective α-deprotonation–rearrangement of cis-cyclooctene oxide 1 using organolithiums in the presence of (–)-sparteine 4 or (–)-α-isosparteine 5 gives the (–)-alcohol 2 in good yields and ees. The use of C₂-symmetric bisoxazolines (–)-6a–d as ligands allows access to the (+)-alcohol 2. (–)-α-Isosparteine 5 functions as an efficient asymmetric ligand catalyst in the rearrangement of 1. The α-deprotonation process can be extended to other cycloalkene-derived achiral epoxides 7, 9, 11, 15 and 19. Lithium amide-induced transformations of rigid bicycloalkene-derived epoxides (25, 34 and 42) are described, providing insight into the rearrangement mechanisms which operate following α-lithiation in such systems. The enantioselective α-deprotonation–rearrangement of bicycloalkene-derived epoxides (25, 29 and 42) to ketones (28, 33 and 44 respectively) is described.

References

1. R. S. Ward, Chem. Soc. Rev., 1990, 30, 1; T.-L. Ho, Symmetry: A Basis For Synthesis Design, Wiley, New York, 1995; E. Schoffers, A. Golebiowski and C. R. Johnson, Tetrahedron, 1996, 52, 3769.
2. (a) P. J. Cox and N. S. Simpkins, Tetrahedron: Asymmetry, 1991, 2, 1; (b) M. Asami, J. Synth. Org. Chem. Jpn., 1996, 54, 188; (c) D. M. Hodgson, A. R. Gibbs and G. P. Lee, Tetrahedron, 1996, 52, 14 361; (d) D. M. Hodgson and A. R. Gibbs, Tetrahedron Lett., 1997, 38, 8907; (e) P. O'Brien, J. Chem. Soc., Perkin Trans. 1, 1998, 1439.
3. Preliminary communications: D. M. Hodgson and G. P. Lee, Chem. Commun., 1996, 1015; D. M. Hodgson and R. Wisedale, Tetrahedron: Asymmetry, 1996, 7, 1275; D. M. Hodgson and R. E. Marriott, Tetrahedron Lett., 1997, 38, 887; D. M. Hodgson and R. E. Marriott, Tetrahedron: Asymmetry, 1997, 8, 519; D. M. Hodgson and G. P. Lee, Tetrahedron: Asymmetry, 1997, 8, 2303.
4. (a) J. K. Crandall and M. Apparu, Org. React. (N.Y.), 1983, 29, 345; (b) T. Satoh, Chem. Rev., 1996, 96, 3303.
5. J. K. Whitesell and P. D. White, Synthesis, 1975, 602.
6. S. Murata, M. Suzuki and R. Noyori, Bull. Chem. Soc. Jpn., 1982, 55, 247.
7. A. Mordini, E. Ben Rayana, C. Margot and M. Schlosser, Tetrahedron, 1990, 46, 2401.
8. R. K. Boeckman, Jr., Tetrahedron Lett., 1977, 4281.
9. (a) D. Hoppe, F. Hintze and P. Tebben, Angew. Chem., Int. Ed. Engl., 1990, 29, 1422; (b) Review: D. Hoppe and T. Hense, Angew. Chem., Int. Ed. Engl., 1997, 36, 2282.
10. J. K. Whitesell, M. A. Minton and S. W. Felman, J. Org. Chem., 1983, 48, 2193.
11. M. Amadji, J. Vadecard, J.-C. Plaquevent, L. Duhamel and P. Duhamel, J. Am. Chem. Soc., 1996, 118, 12 483.
12. P. Beak, S. T. Kerrick, S. Wu and J. Chu, J. Am. Chem. Soc., 1994, 116, 3231.
13. H. Gilman, F. W. Moore and O. Baine, J. Am. Chem. Soc., 1941, 63, 2479; H. Gilman, W. Langham and F. W. Moore, J. Am. Chem. Soc., 1940, 62, 2327.
14. D. J. Gallagher, S. T. Kerrick and P. Beak, J. Am. Chem. Soc., 1992, 114, 5872.
15. J. K. Whitesell, Chem. Rev., 1989, 89, 1581.
16. O. Zschage and D. Hoppe, Tetrahedron, 1992, 48, 5657.
17. J. Kang, W. O. Cho, H. G. Cho and H. J. Oh, Bull. Korean Chem. Soc., 1994, 26, 732.
18. J. Kang, W. O. Cho and H. G. Cho, Tetrahedron: Asymmetry, 1994, 5, 1347; J. Kang, J. I. Kim and J. H. Lee, Bull. Korean Chem. Soc., 1994, 26, 865.
19. D. J. Gallagher, S. Wu, N. A. Nikolic and P. Beak, J. Org. Chem., 1995, 60, 8148.
20. G. Galinovsky, P. Knoth and W. Fischer, Monatsh. Chem., 1955, 86, 1014.
21. T. Ebner, M. Eichelbaum, P. Fischer and C. O. Meese, Arch. Pharm. (Weinheim), 1989, 322, 399.
22. For some exceptions see: P. Beak, A. Bass, D. J. Gallagher, Y. S. Park and S. Thayumanavan, Acc. Chem. Res., 1996, 29, 552.
23. S. E. Denmark, N. Nakajima, O. J.-C. Nicaise, A.-M. Faucher and J. P. Edwards, J. Org. Chem., 1995, 60, 4884.
24. (a) S. E. Denmark, N. Nakajima and O. J.-C. Nicaise, J. Am. Chem. Soc., 1994, 116, 8797; (b) Review: S. E. Denmark and O. J.-C. Nicaise, Chem. Commun., 1996, 999.
25. V. Prelog, K. Schenker and H. H. Gunthard, Helv. Chim. Acta, 1952, 35, 1598.
26. A. I. Meyers, W. N. Beverung and R. Gault, Org. Synth., 1988, Coll. Vol. VI, 371; C. J. Pouchert and J. Behnke, The Aldrich Library of ¹³C and ¹H FT NMR Spectra, Aldrich Chemical, Milwaukee, 1992, vol. 1, 254B.
27. C. Djerassi and J. Staunton, J. Am. Chem. Soc., 1961, 83, 736.
28. K. J. Shea and J.-S. Kim, J. Am. Chem. Soc., 1992, 114, 3044.
29. R. W. Thies and R. H. Chiarello, J. Org. Chem., 1979, 44, 1342.
30. L. L. Adams and F. A. Luzzio, J. Org. Chem., 1989, 54, 5387.
31. D. I. Schuster, J. Woning, N. A. Kaprinidis, Y. Pan, B. Cai, M. Barra and C. A. Rhodes, J. Am. Chem. Soc., 1992, 114, 7029.
32. C. L. Kissel and B. Rickborn, J. Org. Chem., 1972, 37, 2060.
33. T. Baba, K. Avasthi and A. Suzuki, Bull. Chem. Soc. Jpn., 1983, 56, 1571.
34. (a) P. A. Levene and S. A. Harris, J. Biol. Chem., 1935, 112, 195; (b) W. J. Richter, B. Richter and E. Ruch, Angew. Chem., Int. Ed. Engl., 1973, 12, 30.
35. T. Fukazawa and T. Hashimoto, Tetrahedron: Asymmetry, 1993, 4, 2323.
36. J. K. Crandall and L.-H. C. Lin, J. Am. Chem. Soc., 1967, 89, 4526; J. K. Crandall and L.-H. C. Lin, J. Am. Chem. Soc., 1967, 89, 4527; unpublished work cited in ref. 4a, p. 375.
37. (a) E. Doris, L. Dechoux and C. Mioskowski, Tetrahedron Lett., 1994, 35, 7943; (b) C. Mioskowski, personal communication; (c) E. Doris, L. Dechoux and C. Mioskowski, Synlett, 1998, 337.
38. H. Nozaki, T. Mori and R. Noyori, Tetrahedron, 1966, 22, 1207.
39. H. Nozaki and R. Noyori, J. Org. Chem., 1965, 30, 1652.
40. N. Kornblum, A. S. Erickson, W. J. Kelly and B. Henggeler, J. Org. Chem., 1982, 47, 4534.
41. D. M. Hodgson, J. Witherington and B. A. Moloney, J. Chem. Soc., Perkin Trans. 1, 1994, 1543; J.-P. Deprés and A. E. Greene, Org. Synth., 1997, 75, 195.
42. L. A. Spurlock and R. G. Fayter, Jr., J. Am. Chem. Soc., 1972, 94, 2707.
43. N. S. Zefirov, L. I. Kasyan, L. Y. Gnedenkov, A. S. Shashkov and E. G. Cherepanova, Tetrahedron Lett., 1979, 949.
44. (a) J. K. Crandall, J. Org. Chem., 1964, 29, 2830; (b) J. Meinwald, J. Crandall and W. E. Hymans, Org. Synth., 1973, Coll. Vol. V, 863.
45. D. C. Kleinfelter and P. v. R. Schleyer, Org. Synth., 1973, Coll. Vol. V, 852; C. J. Pouchert and J. Behnke, The Aldrich Library of ¹³C and ¹H FT NMR Spectra, Aldrich Chemical, Milwaukee, 1992, vol. 1, 678A.
46. B. J. Bunn and N. S. Simpkins, J. Org. Chem., 1993, 58, 533.
47. (a) W. Kirmse and N. Knöpfel, J. Am. Chem. Soc., 1976, 98, 4672; (b) Y. Hirose, M. Anzai, M. Saitoh, K. Naemura and H. Chikamatsu, Chem. Lett., 1989, 1939.
48. J. K. Crandall, L. C. Crawley, D. B. Banks and L. C. Lin, J. Org. Chem., 1971, 36, 510.
49. A. Yanagisawa, K. Yasue and H. Yamamoto, J. Chem. Soc., Chem. Commun., 1994, 2103.
50. H. C. Brown and S. Krishnamurthy, J. Am. Chem. Soc., 1972, 94, 7159.
51. J. B. Stothers, C. T. Tan and K. C. Teo, Can. J. Chem., 1976, 54, 1211.
52. C. J. Pouchert and J. Behnke, The Aldrich Library of ¹³C and ¹H FT NMR Spectra, Aldrich Chemical, Milwaukee, 1992, vol. 1, 249A.
53. J. A. Berson, J. S. Walia, A. Remanick, S. Suzuki, P. Reynolds-Warnhoff and D. Willner, J. Am. Chem. Soc., 1961, 83, 3986.
54. R. W. Murray, M. K. Pillay and R. Jeyaraman, J. Org. Chem., 1988, 53, 3007; W. Adam, J. Bialas and L. Hadjiarapoglou, Chem. Ber., 1991, 124, 2377.
55. (a) A. O. Chizkov, N. S. Zefirov, N. V. Zyk and T. C. Morrill, J. Org. Chem., 1987, 52, 5647; (b) N. S. Zefirov, personal communication.
56. A. Gagneux and C. A. Grob, Helv. Chim. Acta, 1959, 42, 2006.
57. A. B. Smith III, J. R. Empfield, R. A. Rivero, H. V. Vaccaro, J. J.-W. Duan and M. M. Sulikowski, J. Am. Chem. Soc., 1992, 114, 9419.
58. M. Demuth, S. Chandrasekhar and K. Shaffner, J. Am. Chem. Soc., 1984, 106, 1092.
59. E. Nagano and K. Mori, Biosci. Biotechnol. Biochem., 1992, 56, 1589.
60. R. V. Williams, K. Chauhan and V. J. Gadgil, J. Chem. Soc., Chem. Commun., 1994, 1739.
61. C. Weitemeyer, T. Preuβ and A. de Meijere, Chem. Ber., 1985, 118, 3993.
62. A. H. Hoveyda, D. A. Evans and G. C. Fu, Chem. Rev., 1993, 93, 1307.
63. D. A. Evans, A. M. Golob, N. S. Mandel and G. S. Mandel, J. Am. Chem. Soc., 1978, 100, 8170.
64. (a) A. F. Diaz, M. Sakai and S. Winstein, J. Am. Chem. Soc., 1970, 92, 7477; (b) W. Lotsch and A. S. Kende, Angew. Chem., Int. Ed. Engl., 1971, 10, 559.
65. D. W. Rome and B. J. Johnson, Tetrahedron, 1971, 27, 2271.
66. R. Aumann, H. Wörmann and C. Krüger, Chem. Ber., 1977, 110, 1442.
67. K. Bambridge, M. J. Begley and N. S. Simpkins, Tetrahedron Lett., 1994, 35, 3391.
68. M. A. Dyadchenko, V. I. Mel'nikova and K. K. Pivnitskii, J. Gen. Chem. USSR (Engl. Transl.), 1986, 58, 1891 (Chem. Abstr., 1987, 107, 134 071k).
69. H. Kuritani, S. Imajo, K. Shingo and M. Nakagawa, Tetrahedron Lett., 1979, 19, 1697.
70. D. A. Dickman, A. I. Meyers, G. A. Smith and R. E. Gawley, Org. Synth., 1990, Coll. Vol. VII, 530.
71. M. Ohno and M. Okamoto, Org. Synth., 1973, Coll. Vol. V, 281.
72. G. C. Overberger, N. P. Marullo and R. G. Hiskey, J. Am. Chem. Soc., 1961, 94, 1374; C. M. Cain, R. P. C. Cousins, G. Coumbarides and N. S. Simpkins, Tetrahedron, 1990, 46, 523 [(S,S)-Bis(1-phenylethyl)amine is now available commercially (Oxford Asymmetry or Aldrich).].
73. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori and M. Camalli, J. Appl. Crystallogr., 1992, 27, 435.
74. J. R. Carruthers and D. J. Watkin, Acta Crystallogr., Sect. A, 1979, 35, 698.
75. D. J. Watkin, J. R. Carruthers and W. Betteridge, CRYSTALS User Guide, Chemical Crystallography Laboratory, Oxford, 1985; L. J. Pearce, K. Prout and D. J. Watkin, CAMERON User Guide, Chemical Crystallography Laboratory, Oxford, 1994; D. T. Cromer and J. T. Weber, International Tables for X-ray Crystallography, eds. J. A. Ibers and W. C. Hamilton, Kynoch Press, Birmingham, 1974, vol. 4.