Stereocontrolled route to some optically active β-hydroxy phosphine oxides using the stereoselective addition of metallated phosphine oxides to proline-derived keto aminals

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 17, 1996, Pages 2117-2127

  O'Brien, Peter ^a   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748976542     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960002117     Document Type: Article

References (60)

1. J. Clayden, E. W. Collington and S. Warren, Tetrahedron Lett., 1993, 34, 1327.
2. J. Clayden, E. W. Collington, R. B. Lamont and S. Warren, Tetrahedron Lett., 1993, 34, 2203.
3. N. J. S. Harmat and S. Warren, Tetrahedron Lett., 1990, 31, 2743.
4. J. Clayden, A. B. McElroy and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1995, 1913.
5. J. Clayden and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1994, 2811.
6. (a) B. E. Rossiter, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, 1985, vol. 5, ch. 7, p. 212;
7. (b) M. G. Finn and K. B. Sharpless, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, 1985, vol. 5, ch. 8, p. 247;
8. (c) R. A. Johnson and K. B. Sharpless, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, New York, 1991, vol. 7, ch. 3.2, p. 389.
9. A. Nelson, P. O'Brien and S. Warren, Tetrahedron Lett., 1995, 36, 2685.
10. H. C. Kolb, M. S. VanNieuwenhze and K. B. Sharpless, Chem. Rev., 1994, 94, 2483.
11. A. D. Buss and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1985, 2307.
12. J. Clayden and S. Warren, Angew. Chem., Int. Ed. Engl., 1996, 35, 241.
13. J. E. Lynch and E. L. Eliel, J. Am. Chem. Soc., 1984, 106, 2943.
14. X.-C. He and E. L. Eliel, Tetrahedron, 1987, 43, 4979.
15. Y. Ukaji, K. Yamamoto, M. Fukui and T. Fujisawa, Tetrahedron Lett., 1991, 32, 2919.
16. A. Alexakis, N. Lensen and P. Mangeney, Tetrahedron Lett., 1991, 32, 1171.
17. T. Mukaiyama, Tetrahedron, 1981, 37, 4111.
18. Preliminary communication: P. O'Brien and S. Warren, Tetrahedron Lett., 1995, 36, 2681.
19. For some alternative approaches to the same types of compounds, see: P. O'Brien and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1996, following paper.
20. (a) K. C. Frieboes, T. Harder, D. Aulbert, C. Strahringer, M. Bolte and D. Hoppe, Synlett, 1993, 921;
21. (b) T. Harder, T. Löhl, M. Bolte, K. Wagner and D. Hoppe, Tetrahedron Lett., 1994, 35, 7365.
22. G. Poli, E. Maccagni, L. Manzoni, T. Pilati and C. Scolastico, Synlett, 1995, 71.
23. For reductions of keto oxazolidines, see: L. Manzoni, T. Pilati, G. Poli and C. Scolastico, J. Chem. Soc., Chem. Commun., 1992, 1027.
24. (a) C. Agami, F. Couty and C. Lequesne, Tetrahedron Lett., 1994, 35, 3309;
25. (b) C. Agami, F. Couty and C. Lequesne, Tetrahedron, 1995, 51, 4043.
26. (a) L. Colombo, M. Di Giacomo, G. Brusotti and G. Delogu, Tetrahedron Lett., 1994, 35, 2063;
27. (b) L. Colombo, M. Di Giacomo, G. Brusotti and E. Milano, Tetrahedron Lett., 1995, 36, 2863.
28. For examples of the use of Mukaiyama's aminal methodology in total synthesis, see: (a) (+)- and (-)-frontalin; Y. Sakito and T. Mukaiyama, Chem. Lett., 1979, 1027;
29. (b) (-)-malyngolide; Y. Sakito, S. Tanaka, M. Asami and T. Mukaiyama, Chem. Lett., 1980, 1223;
30. (c) exo-(+)-brevicomin; M. Asami and T. Mukaiyama, Chem. Lett., 1983, 93.
31. T. Mukaiyama, Y. Sakito and M. Asami, Chem. Lett., 1978, 1253.
32. T. Mukaiyama, Y. Sakito and M. Asami, Chem. Lett., 1979, 705.
33. Y. Sakito, M. Asami and T. Mukaiyama, Chem. Lett., 1980, 455.
34. D. J. Cram and F. A. Abd Elhafez, J. Am. Chem. Soc., 1952, 74, 5828.
35. (a) M. Chérest, H. Felkin and N. Prudent, Tetrahedron Lett., 1968, 2199;
36. (b) M. Chérest and N. Prudent, Tetrahedron, 1980, 36, 1599.
37. Diamine (S)-8 [(S)-(+)-2-(anilinomethyl)pyrrolidine] is available from Aldrich Chemical Company Limited.
38. M. Asami, H. Ohno, S. Kobayashi and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1978, 51, 1869.
39. J. Hook, Synth. Commun., 1984, 14, 83.
40. For Weinreb's amide methodology, see: (a) S. Nahm and S. M. Weinreb, Tetrahedron Lett., 1981, 22, 3815;
41. (b) B. T. O'Neill, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, New York, 1991, vol. 1, p. 397;
42. M. F. Lipton, A. Basha and S. M. Weinreb, Org. Synth., 1988, 59, 49.
43. Agami has used a similar Weinreb amide approach to synthesise some keto oxazolidines (see ref. 19).
44. H. R. Powell and P. R. Raithby, personal communication.
45. W. C. Still and J. H. McDonald III, Tetrahedron Lett., 1980, 21, 1031.
46. S. Mori, M. Nakamura, E. Nakamura, N. Koga and K. Morokuma, J. Am. Chem. Soc., 1995, 117, 5055.
47. T. Imamoto, T. Kusumoto, Y. Tawarayama, Y. Sugiuara, T. Mita, Y. Hatanaka and M. Yokoyama, J. Org. Chem., 1984, 49, 3904.
48. M. T. Reetz, S. H. Kyung and M. Hüllmann, Tetrahedron, 1986, 42, 2931.
49. D. Seyferth, D. E. Welch and J. K. Heeren, J. Am. Chem. Soc., 1964, 86, 1100.
50. Lithium to magnesium transmetallation using magnesium bromide has been reported previously for a number of related heteroatom-stabilised organolithiums: (a) alkyl sulfones; P. J. Kocienski, B. Lythgoe and S. Ruston, J. Chem. Soc., Perkin Trans. 1, 1978, 829;
51. (b) alkyl silanes; K. Tamao, R. Kanatani and M. Kumada, Tetrahedron Lett., 1984, 25, 1913;
52. (c) vinyl sulfones; J. J. Eisch and J. E. Galle, J. Org. Chem., 1979, 44, 3279;
53. (d) vinylsilanes; J. E. Wrobel and B. Ganem, J. Org. Chem., 1983, 48, 3761.
54. For other interesting lithium halide effects, see: (a) D. Seebach, Angew. Chem., Int. Ed. Engl., 1988, 27, 1624;
55. (b) K. Rück, Angew. Chem., Int. Ed. Engl., 1995, 34, 433;
56. B. J. Bunn and N. S. Simpkins, J. Org. Chem., 1993, 58, 533.
57. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.
58. A. Berger, J. Kurtz and E. Katchalski, J. Am. Chem. Soc., 1954, 74, 5552.
59. B. S. Furniss, A. J. Hannaford, P. W. G. Smith and A. R. Tatchell, Vogel's Textbook of Practical Organic Chemistry, Longman, Wiley, New York, 5th edn., 1989, p. 763.
60. M. E. Jung, K. Shishido and L. H. Davis, J. Org. Chem., 1982, 47, 891.