Reactions of electrophilic carbenes with α-amino acid derivatives

Tetrahedron

Volumn 53, Issue 10, 1997, Pages 3425-3439

  Zaragoza, Florencio ^a  

^a NOVO NORDISK A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

DRUG SYNTHESIS; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW;

EID: 0031562379     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01170-2     Document Type: Review

References (75)

1. 1. Crosby, J. Tetrahedron 1991, 47, 4789-4846.
2. 2. Ager, D. J.; Prakash, I.; Schadd, D. R. Chem. Rev. 1996, 96, 835-875.
3. 3. Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650.
4. 4. Williams, R. M. (Synthesis of Optically Active Alpha-Amino Acids Organic Chemistry Series, vol. 7), Pergamon Press, Oxford, 1989.
5. 5. Recent reviews covering different aspects of synthetic carbene chemistry: a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223-269;
6. b) Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811-10843;
7. c) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160;
8. d) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453;
9. e) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765-1808;
10. f) Padwa, A.; Hombuckle, S. F. Chem. Rev. 1991, 91, 263-309.
11. 6. The reactions of α-amino acid-derived 3-amino-1-diazo ketones are not covered in this review.
12. 7. Stork, G.; Nakatani, K. Tetrahedron Lett. 1988, 29, 2283-2286.
13. 8. Adams, J.; Poupart, M.-A.; Grenier, L.; Schaller, C.; Ouimet, N.; Frenette, R. Tetrahedron Lett. 1989, 30, 1749-1752.
14. 9. Ballabio, M.; Malatesta, V.; Ruggieri, D.; Temperelli, A. Gazz. Chim. Ital. 1988, 118, 375-383.
15. 10. α-Alkylation of α-amino acids by carbene C-H insertion may lead to enantiomerically pure products. Several examples for carbene C-H insertion with retention of configuration at the alkylated carbon atom have been reported. See e.g. Monteiro, H. J.; Zuckerman-Schpector, J. Tetrahedron 1996, 52, 3879-3888; Lee, E.; Choi, I.; Song, S. Y. J. Chem. Soc., Chem. Commun. 1995, 321-322; Taber, D. F.; Petty, E. H.; Raman K. J. Am. Chem. Soc. 1985, 107, 196-199.
16. 10. α-Alkylation of α-amino acids by carbene C-H insertion may lead to enantiomerically pure products. Several examples for carbene C-H insertion with retention of configuration at the alkylated carbon atom have been reported. See e.g. Monteiro, H. J.; Zuckerman-Schpector, J. Tetrahedron 1996, 52, 3879-3888; Lee, E.; Choi, I.; Song, S. Y. J. Chem. Soc., Chem. Commun. 1995, 321-322; Taber, D. F.; Petty, E. H.; Raman K. J. Am. Chem. Soc. 1985, 107, 196-199.
17. 10. α-Alkylation of α-amino acids by carbene C-H insertion may lead to enantiomerically pure products. Several examples for carbene C-H insertion with retention of configuration at the alkylated carbon atom have been reported. See e.g. Monteiro, H. J.; Zuckerman-Schpector, J. Tetrahedron 1996, 52, 3879-3888; Lee, E.; Choi, I.; Song, S. Y. J. Chem. Soc., Chem. Commun. 1995, 321-322; Taber, D. F.; Petty, E. H.; Raman K. J. Am. Chem. Soc. 1985, 107, 196-199.
18. 11. Doyle, M. P.; Taunton, J.; Pho, H. Q. Tetrahedron Lett. 1989, 30, 5397-5400.
19. 12. Wee, A. G. H.; Liu, B.; Zhang, L. J. Org. Chem. 1992, 57, 4404-4414.
20. 13. Zaragoza, F. Tetrahedron 1995, 51, 8829-8834.
21. 4. The canonical form A will only contribute to a negligible extent to the structure of the intermediate formed from diazocarbonyl compounds and rhodium carboxylates (cf. Figure 4). A would be relevant only for electron-rich catalysts M, which on the other hand would not be able to react with the weakly nucleophilic diazo compounds. Moreover, if A contributes significantly to the structure of the intermediate, then this species should behave chemically as a (stabilized) ylide and not as a carbene. Ylides normally do not give carbene-type reactions, unless subjected to photolysis or pyrolysis.
22. 15. Ko, K.-Y.; Lee, K.-I.; Kim, W.-J. Tetrahedron Lett. 1992, 33, 6651-6652.
23. 16. Zaragoza, F.; Ullmann, A.; unpublished results.
24. 17. Chowdhry, V.; Vaughan, R.; Westheimer, F. Proc. Nat. Acad. Sci. USA 1976, 73, 1406-1408.
25. 18. Tomioka, H.; Suzuki, K. Tetrahedron Lett. 1989, 30, 6353-6356.
26. 19. Zaragoza, F.; Zahn, G. J. Prakt. Chem. 1995, 337, 292-298.
27. 20. Bright, G. M.; Dee, M. F.; Kellogg, M. S. Heterocycles 1980, 14, 1251-1254.
28. 21. Backes, J. Houben-Weyl, 4th ed., Vol. E16b; Klamann, D., Ed.; Thieme, Stuttgart, 1991; pp. 192-198.
29. 22. Rando, R. R. J. Am. Chem. Soc. 1970, 92, 6706-6707.
30. 23. Doyle, M. P.; Pieters, R. J.; Taunton, J.; Pho, H. Q. J. Org. Chem. 1991, 56, 820-829.
31. 24. Doyle, M. P.; Oon, S.-M.; van der Heide, F. R.; Brown, C. B. Bioorg. Med. Chem. Lett. 1993, 3, 2409-2414.
32. 25. Corey, E. J.; Felix, A. M. J. Am. Chem. Soc. 1965, 87, 2518-2519.
33. 26. Lowe, G.; Parker, J. J. Chem. Soc., Chem. Commun. 1971, 577-578.
34. 27. Brunwin, D. M.; Lowe, G.; Parker, J. J. Chem. Soc. C 1971, 3756-3762.
35. 28. Brunwin, D. M.; Lowe, G. J. Chem. Soc., Chem. Commun. 1972, 589-590.
36. 29. Doyle, M. P.; Dyatkin, A. B.; Autry, C. L. J. Chem. Soc., Perkin Trans. 1, 1995, 619-621.
37. 30. a) Paulissen, R.; Hayez, E.; Hubert, A.; Teyssié, P. Tetrahedron Lett. 1974, 607-608;
38. b) Paulissen, R.; Reimlinger, H.; Hayez, E.; Hubert, A. J.; Teyssié, P. Tetrahedron Lett. 1973, 2233-2236.
39. 31. Häbich, D.; Hartwig, W. Tetrahedron 1984, 40, 3667-3676.
40. 32. Osipov, S. N.; Sewald, N.; Kolomiets, A. F.; Fokin, A. V.; Burger, K. Tetrahedron Lett. 1996, 37, 615-618.
41. 33. Backes, J. Houben-Weyl, 4th ed., Vol. E16b; Klamann, D., Ed.; Thieme, Stuttgart, 1991; pp. 591-602.
42. 34. Adams, D. R.; Bailey, P. D.; Collier, I. D.; Heffernan, J. D.; Stockes, S. J. Chem. Soc., Chem. Commun. 1996, 349-350.
43. 35. Honma, T.; Tada, Y.; Adachi, I.; Igarashi, K. J. Heterocycl. Chem. 1989, 26, 629-634.
44. 36. Baldwin, J. E.; Adlington, R. M.; Godfrey, C. R. A.; Gollins, D. W.; Vaughan, J. G. J. Chem. Soc., Chem. Commun. 1993, 1434-1435.
45. 37. Baldwin, J. E.; Adlington, R. M.; Godfrey, C. R. A.; Gollins, D. W.; Smith, M. L.; Russel, A. T. Synlett 1993, 51-53.
46. 38. Burger, K.; Rudolph, M.; Fehn, S. Angew. Chem. 1993, 105, 293-295; Angew. Chem., Int. Ed. Engl. 1993, 32, 285-287.
47. 38. Burger, K.; Rudolph, M.; Fehn, S. Angew. Chem. 1993, 105, 293-295; Angew. Chem., Int. Ed. Engl. 1993, 32, 285-287.
48. 39. Pine, S. H. Org. React. 1970, 18, 403-466.
49. 40. Ollis, W. D.; Rey, M.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1983, 1009-1027.
50. 41. West, F. G.; Glaeske, K. W.; Naidu, B. N. Synthesis 1993, 977-980.
51. 42. West, F. G.; Naidu, B. N. J. Am. Chem. Soc. 1993, 115, 1177-1178.
52. 43. West, F. G.; Naidu, B. N. J. Am. Chem. Soc. 1994, 116, 8420-8421.
53. 44. Zaragoza, F. Synlett 1995, 237-238.
54. 45. Pellicciari, R.; Natalini, B.; Marinozzi, M.; Monahan, J. B.; Snyder, J. P. Tetrahedron Lett. 1990, 31, 139-142.
55. 46. Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y. J. Org. Chem. 1991, 56, 4167-4176; Kurokawa, N.; Ohfune, Y. Tetrahedron Lett. 1985, 26, 83-84.
56. 46. Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y. J. Org. Chem. 1991, 56, 4167-4176; Kurokawa, N.; Ohfune, Y. Tetrahedron Lett. 1985, 26, 83-84.
57. 47. Dappen, M. S.; Pellicciari, R.; Natalini, B.; Monahan, J. B.; Chiorri, C.; Cordi, A. A. J. Med. Chem. 1991, 34, 161-168.
58. 48. Yoshimoto, M.; Ishihara, S.; Nakayama, E.; Shoji, E.; Kuwano, H.; Soma, N. Tetrahedron Lett. 1972, 4387-4390.
59. 49. Kametani, T.; Kanaya, N.; Mochizuki, T.; Honda, T. Heterocycles 1983, 20, 435-436; Kametani, T.; Kanaya, N.; Mochizuki, T.; Honda, T. Tetrahedron Lett. 1983, 24, 1511-1512.
60. 49. Kametani, T.; Kanaya, N.; Mochizuki, T.; Honda, T. Heterocycles 1983, 20, 435-436; Kametani, T.; Kanaya, N.; Mochizuki, T.; Honda, T. Tetrahedron Lett. 1983, 24, 1511-1512.
61. 50. Morin, J. M.; Spry, D. O.; Elzey, T. K.; Kinnick, M. D.; Paschal, J. W.; Snyder, N. J. Heterocycles 1990, 31, 1423-1426.
62. 51. Wang, H. C.; Lee, Y. Y.; Goo, Y. M. J. Korean Chem. Soc. 1992, 36, 157-160; Kametani, T.; Kanaya, N.; Nakayama, A.; Mochizuki, T.; Yokohama, S.; Honda, T. J. Org. Chem. 1986, 51, 624-629; Numata, M.; Imashiro, Y.; Minamida, I.; Yamaoka, M. Tetrahedron Lett. 1972, 5097-5100; Yoshimoto, M.; Ishihara, S.; Nakayama, E.; Soma, N. Tetrahedron Lett. 1972, 2923-2926.
63. 51. Wang, H. C.; Lee, Y. Y.; Goo, Y. M. J. Korean Chem. Soc. 1992, 36, 157-160; Kametani, T.; Kanaya, N.; Nakayama, A.; Mochizuki, T.; Yokohama, S.; Honda, T. J. Org. Chem. 1986, 51, 624-629; Numata, M.; Imashiro, Y.; Minamida, I.; Yamaoka, M. Tetrahedron Lett. 1972, 5097-5100; Yoshimoto, M.; Ishihara, S.; Nakayama, E.; Soma, N. Tetrahedron Lett. 1972, 2923-2926.
64. 51. Wang, H. C.; Lee, Y. Y.; Goo, Y. M. J. Korean Chem. Soc. 1992, 36, 157-160; Kametani, T.; Kanaya, N.; Nakayama, A.; Mochizuki, T.; Yokohama, S.; Honda, T. J. Org. Chem. 1986, 51, 624-629; Numata, M.; Imashiro, Y.; Minamida, I.; Yamaoka, M. Tetrahedron Lett. 1972, 5097-5100; Yoshimoto, M.; Ishihara, S.; Nakayama, E.; Soma, N. Tetrahedron Lett. 1972, 2923-2926.
65. 51. Wang, H. C.; Lee, Y. Y.; Goo, Y. M. J. Korean Chem. Soc. 1992, 36, 157-160; Kametani, T.; Kanaya, N.; Nakayama, A.; Mochizuki, T.; Yokohama, S.; Honda, T. J. Org. Chem. 1986, 51, 624-629; Numata, M.; Imashiro, Y.; Minamida, I.; Yamaoka, M. Tetrahedron Lett. 1972, 5097-5100; Yoshimoto, M.; Ishihara, S.; Nakayama, E.; Soma, N. Tetrahedron Lett. 1972, 2923-2926.
66. 52. Zaragoza, F.; Petersen, S. V. Tetrahedron 1996, 52, 10823-10826; Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811-10843; Shi, G.; Cao, Z.; Cai, W. Tetrahedron 1995, 51, 5011-5018; Aller, E.; Brown, D. S.; Cox, G. G.; Miller, D. J.; Moody, C. J. J. Org. Chem. 1995, 60, 4449-4460; Cox, G. G.; Miller, D. J.; Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195-3212; Haigh, D. Tetrahedron 1994, 50, 3177-3194.
67. 52. Zaragoza, F.; Petersen, S. V. Tetrahedron 1996, 52, 10823-10826; Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811-10843; Shi, G.; Cao, Z.; Cai, W. Tetrahedron 1995, 51, 5011-5018; Aller, E.; Brown, D. S.; Cox, G. G.; Miller, D. J.; Moody, C. J. J. Org. Chem. 1995, 60, 4449-4460; Cox, G. G.; Miller, D. J.; Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195-3212; Haigh, D. Tetrahedron 1994, 50, 3177-3194.
68. 52. Zaragoza, F.; Petersen, S. V. Tetrahedron 1996, 52, 10823-10826; Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811-10843; Shi, G.; Cao, Z.; Cai, W. Tetrahedron 1995, 51, 5011-5018; Aller, E.; Brown, D. S.; Cox, G. G.; Miller, D. J.; Moody, C. J. J. Org. Chem. 1995, 60, 4449-4460; Cox, G. G.; Miller, D. J.; Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195-3212; Haigh, D. Tetrahedron 1994, 50, 3177-3194.
69. 52. Zaragoza, F.; Petersen, S. V. Tetrahedron 1996, 52, 10823-10826; Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811-10843; Shi, G.; Cao, Z.; Cai, W. Tetrahedron 1995, 51, 5011-5018; Aller, E.; Brown, D. S.; Cox, G. G.; Miller, D. J.; Moody, C. J. J. Org. Chem. 1995, 60, 4449-4460; Cox, G. G.; Miller, D. J.; Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195-3212; Haigh, D. Tetrahedron 1994, 50, 3177-3194.
70. 52. Zaragoza, F.; Petersen, S. V. Tetrahedron 1996, 52, 10823-10826; Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811-10843; Shi, G.; Cao, Z.; Cai, W. Tetrahedron 1995, 51, 5011-5018; Aller, E.; Brown, D. S.; Cox, G. G.; Miller, D. J.; Moody, C. J. J. Org. Chem. 1995, 60, 4449-4460; Cox, G. G.; Miller, D. J.; Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195-3212; Haigh, D. Tetrahedron 1994, 50, 3177-3194.
71. 52. Zaragoza, F.; Petersen, S. V. Tetrahedron 1996, 52, 10823-10826; Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811-10843; Shi, G.; Cao, Z.; Cai, W. Tetrahedron 1995, 51, 5011-5018; Aller, E.; Brown, D. S.; Cox, G. G.; Miller, D. J.; Moody, C. J. J. Org. Chem. 1995, 60, 4449-4460; Cox, G. G.; Miller, D. J.; Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195-3212; Haigh, D. Tetrahedron 1994, 50, 3177-3194.
72. 53. Teng, C.-Y. P.; Ganem, B.; Doktor, S. Z.; Nichols, B. P.; Bhatnagar, R. K.; Vining, L. C. J. Am. Chem. Soc. 1985, 107, 5008-5009.
73. 54. Palmer, M. J.; Danilewicz, J. C.; Vuong, H. Synlett 1994, 171-172; Ho, M.; Wang, W.; Douvlos, M.; Pham, T.; Klock, T. Tetrahedron Lett. 1991, 32, 1283-1286.
74. 54. Palmer, M. J.; Danilewicz, J. C.; Vuong, H. Synlett 1994, 171-172; Ho, M.; Wang, W.; Douvlos, M.; Pham, T.; Klock, T. Tetrahedron Lett. 1991, 32, 1283-1286.
75. 55. Hlavácek, J.; Král, V. Collect. Czech. Chem. Commun. 1992, 57, 525-530.