Recent advances in stereoselective synthesis involving diazocarbonyl intermediates

Chemical Communications

Volumn , Issue 11, 1997, Pages 983-989

  Doyle, Michael P ^a,c,d,e   McKervey, M Anthony ^b,f,g,h  

^a TRINITY UNIVERSITY   (United States)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

^c IOWA STATE UNIVERSITY   (United States)

^d UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^e HOPE COLLEGE   (United States)

^f MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^g UNIVERSITY COLLEGE CORK   (Ireland)

^h School of Chemistry

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002232648     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (61)

1. W. Burns, M. A. McKervey, T. R. B. Mitchell and J. J. Rooney, J. Am. Chem. Soc., 1978, 100, 906.
2. For a recent review of applications of diazocarbonyl intermediates in organic synthesis see Tao Ye and M. A. McKervey, Chem. Rev., 1994, 94, 1091.
3. For a recent quantitative assessment of the hazards associated with the use of diazotransfer reagents see F. W. Bollinger and L. D. Tuma, Synlett. 1996, 407.
4. L. D. Cama and B. G. Christensen, Tetrahedron Lett., 1978, 4233; T. N. Salzmann, R. W. Ratcliffe, B. G. Christensen and F. A. Bouffard, J. Am. Chem. Soc., 1980, 102, 6161.
5. L. D. Cama and B. G. Christensen, Tetrahedron Lett., 1978, 4233; T. N. Salzmann, R. W. Ratcliffe, B. G. Christensen and F. A. Bouffard, J. Am. Chem. Soc., 1980, 102, 6161.
6. For a comprehensive account of catalysed asymmetric cyclopropanation up to 1985, see G. Maas, Top Curr. Chem., 1987, 137, 75.
7. T. Aratani, Y. Yoneyoshi and T. Nagase, Tetrahedron Lett., 1975, 1707; T. Aratani, Y. Yoneyoshi and T. Nagase, Tetrahedron Lett., 1982, 23, 685.
8. T. Aratani, Y. Yoneyoshi and T. Nagase, Tetrahedron Lett., 1975, 1707; T. Aratani, Y. Yoneyoshi and T. Nagase, Tetrahedron Lett., 1982, 23, 685.
9. D. Muller, G. Umbricht, B. Weber and A. Pfaltz, Helv. Chim. Acta, 1991, 74, 232.
10. R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 1991, 32, 7373.
11. D. A. Evans, K. A. Woerpel and M. M. Hinman, J. Am. Chem. Soc., 1991, 113, 726.
12. K. Ito and T. Katsuki, Tetrahedron Lett., 1993, 34, 2661.
13. R. Paulissen, H. Reimlinger, E. Hayez, A. J. Hubert and P. Teyssie, Tetrahedron Lett., 1973, 2233; A. F. Noels, D. N. Petiniot, A. J. Hubert and Ph. Teyssie, Tetrahedron Lett., 1982, 38, 2733.
14. R. Paulissen, H. Reimlinger, E. Hayez, A. J. Hubert and P. Teyssie, Tetrahedron Lett.. 1973, 2233; A. F. Noels, D. N. Petiniot, A. J. Hubert and Ph. Teyssie, Tetrahedron Lett., 1982, 38, 2733.
15. H. Brunner, H. Kluschanzoff and K. Wutz, Bull. Soc. Chem. Belg., 1989, 98, 63.
16. S. Hashimoto, N. Watanabe and D. Ikegami, Tetrahedron Lett., 1990, 31, 5173.
17. M. Kennedy and M. A. McKervey, J. Chem. Soc., Chem. Commun., 1988, 1028; M. Kennedy, M. A. McKervey, A. R. Maguire and G. H. P. Roos, J. Chem. Soc., Chem. Commun., 1990, 361.
18. M. Kennedy and M. A. McKervey, J. Chem. Soc., Chem. Commun., 1988, 1028; M. Kennedy, M. A. McKervey, A. R. Maguire and G. H. P. Roos, J. Chem. Soc., Chem. Commun., 1990, 361.
19. P. A. Agaskar, F. A. Cotton, L. R. Falvello and S. Han, J. Am. Chem. Soc., 1986, 108, 1214.
20. M. A. McKervey and Tao Ye, J. Chem. Sov., Chem. Commun., 1992, 823; Tao Ye, C. Fernandez Garcia and M. A. McKervey, J. Chem. Soc., Perkin Trans. 1, 1995, 1373.
21. M. A. McKervey and Tao Ye, J. Chem. Sov., Chem. Commun., 1992, 823; Tao Ye, C. Fernandez Garcia and M. A. McKervey, J. Chem. Soc., Perkin Trans. 1, 1995, 1373.
22. M. A. McKervey and N. McCarthy, unpublished results.
23. N. McCarthy, M. A. McKervey, T. Ye, M. McCann, E. Murphy and M. P. Doyle, Tetrahedron Lett., 1992, 33, 5983.
24. G. H. P. Roos and M. A. McKervey, Synth. Commun., 1992, 22, 1751.
25. H. M. L. Davies and D. K. Hutcheson, Tetrahedron Lett., 1993, 34, 7243.
26. E. J. Corey and T. G. Grant, Tetrahedron Lett., 1994, 35, 5373.
27. H. M. L. Davies, P. Bruzinski, D. H. Lake, N. Kong and M. J. Fall, J. Am. Chem. Soc., 1996, 118, 6897.
28. M. P. Doyle, Q.-L. Zhou, C. Charnsangavej, M. A. Longoria, M. A. McKervey and C. F. Garcia, Tetrahedron Lett., 1996, 37, 4129.
29. M. P. Doyle, W. R. Winchester, J. A. A. Hoorn, V. Lynch, S. H. Simonsen and R. Ghosh, J. Am. Chem. Soc., 1993, 115, 9968.
30. M. P. Doyle, A. B. Dyatkin, M. N. Protopopova, C. I. Yang, C. S. Miertschin and W. R. Winchester, Rec. Trav. Chim. Pays-Bas (Chirality Issue, Invited Contribution). 1995, 114, 163.
31. M. P. Doyle, Q.-L. Zhou, C. E. Raab, G. H. P. Roos, S. H. Simonsen and V. Lynch, Inorg. Chem., 1996, 35, 6064.
32. M. P. Doyle, R. E. Austin, A. S. Bailey, M. P. Dwyer, A. B. Dyatkin, A. V. Kalinin, M. M. Y. Kwan, S. Liras, C. J. Oalmann, R. J. Pieters, M. N. Protopopova, C. E. Raab, G. H. P. Roos, Q.-L. Zhou and S. F. Martin, J. Am. Chem. Soc. 1995, 117, 5763.
33. M. P. Doyle and A. V. Kalinin, J. Org. Chem., 1996, 61, 2179.
34. S. F. Martin, R. E. Austin, C. J. Oalmann, W. R. Baker, S. L. Condon, E. DeLara, S. H. Rosenberg, K. P. Spina, H. H. Stein, J. Cohen and H. D. Kleinert, J. Med. Chem., 1992, 35, 1710.
35. S. F. Martin, C. J. Oalmann and S. Liras, Tetrahedron, 1993, 49, 3521.
36. D. H. Rogers, E. C. Yi and C. D. Poulter, J. Org. Chem., 1995, 60, 941.
37. M. P. Doyle, C. S. Peterson, Q.-L. Zhou and H. Nishiyama, Chem. Commun., 1997, 211.
38. J. W. Bode, M. P. Doyle, M. N. Protopopova and Q.-L. Zhou, J. Org. Chem., 1996, 61, 9146.
39. M. P. Doyle, A. B. Dyatkin and J. S. Tedrow, Tetrahedron Lett., 1994, 35, 3853.
40. M. P. Doyle, Q.-L. Zhou, A. B. Dyatkin and D. A. Ruppar, Tetrahedron Lett., 1995, 36, 7579.
41. M. P. Doyle, A. B. Dyatkin, G. H. P. Roos, F. Canas, D. A. Pierson, A. van Basten, P. Muller and P. Polleux, J. Am. Chem. Soc., 1994, 116, 4507.
42. M. P. Doyle and A. V. Kalinin, Tetrahedron Lett., 1996, 37, 1371.
43. M. P. Doyle, A. V. Kalinin and D. G. Ene, J. Am. Chem. Soc., 1996, 118, 8837.
44. M. P. Doyle, M. N. Protopopova, P. Muller, D. Ene and E. A. Shapiro, J. Am. Chem. Soc., 1994, 116, 8492.
45. M. P. Doyle and A. V. Kalinin, Synlett, 195, 1075.
46. E. Aller, D. S. Browne, G. G. Cox, D. J. Miller and C. J. Moody, J. Org. Chem., 1995, 60, 4449.
47. C. F. Garcia, M. A. McKervey and Tao Ye, Chem. Commun., 1966, 1465.
48. R. T. Buck, M. P. Doyle, M. J. Drysdale, L. Ferris, D. C. Forbes, D. Haigh, C. J. Moody, N. D. Pearson and Q.-L. Zhou, Tetrahedron Lett., 1996, 37, 7631.
49. Tao Ye and M. A. McKervey, Tetrahedron, 1992, 48, 8007.
50. R. E. Shute, B. Dunlap and D. H. Rich, J. Med. Chem., 1987, 30, 71.
51. M. A. McKervey, M. B. O'Sullivan, P. L. Myers and R. H. Green, J. Chem. Soc., Chem. Commun., 1993, 94.
52. J. C. Collins, B. M,. Dilworth, N. T. Garvey, M. Kennedy, M. A. McKervey and M. B. O'Sullivan, J. Chem. Soc., Chem. Commun., 1990, 362.
53. M. A. McKervey, D. N. Russell and M. F. Twohig, J. Chem. Soc., Chem. Commun., 1985, 491.
54. M. A. McKervey and M. B. O'Sullivan, unpublished observations.
55. P. Darkins, N. McCarthy, M. A. McKervey, K. O'Donnell, Tao Ye and B. Walker, Tetrhaedron: Asymmetry, 1994, 5, 195.
56. J. Podlech and D. Seebach, Angew. Chem., Int. Ed. Engl., 1995, 34, 471.
57. (a) M. A. McKervey, B. Dilworth and J. C. Collins, unpublished work;
58. (b) S. Hanessian, J.-M. Fu, J.-L. Chiara and R. Di Fabio, Tetrahedron Lett., 1993, 34, 4157;
59. (c) J. Podlech and D. Seebach, Helv. Chim. Acta, 1995, 78, 1238.
60. P. Darkins, N. McCarthy, M. A. McKervey and Tao Ye, J. Chem. Soc., Chem. Commun., 1993, 1222.
61. B. Walker, N. McCarthy, A. Healy, Tao Ye and M. A. McKervey, Biochem. J., 1993, 293, 321.