Asymmetric electrophilic α-amination of carbonyl groups

European Journal of Organic Chemistry

Volumn , Issue 7, 2004, Pages 1377-1385

  Greck, Christine ^a   Drouillat, Bruno ^a   Thomassigny, Christine ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

Amino acids; Asymmetric synthesis; Azodicarboxylate; Chiral catalysts; Electrophilic amination; Stereoselectivity

Indexed keywords

CARBONYL DERIVATIVE; NITROGEN; REAGENT;

AMINATION; AMINO ACID SYNTHESIS; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; REACTION ANALYSIS; SHORT SURVEY; STEREOCHEMISTRY;

EID: 4544370536     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300657     Document Type: Short Survey

References (103)

1. Reviews and references cited therein: [1a] E. Erdik, M. Ay, Chem. Rev. 1989, 89, 1947-1980.
2. [1b] J. Mulzer, Organic Synthesis Highlights, Wiley-VCH, Weinheim, 1991, pp. 45-53.
3. [1c] G. Boche, Stereoselective Synthesis (Houben-Weyl) 1995, Vol. E21, pp. 5133-5157.
4. [1d] C. Greck, J. P. Genet, Synlett 1997, 741-748.
5. [1e] J. P. Genet, C. Greck, D. Lavergne, Modern Amination Methods (Ed.: A. Ricci), Wiley-VCH, Weinheim, 2000, pp. 65-102.
6. [1f] P. Dembech, G. Seconi, A. Ricci, Chem. Eur. J. 2000, 6, 1281-1286.
7. P. Magnus, L. Barth, Tetrahedron 1995, 51, 11075-11086.
8. Y. Niwa, K. Takayama, M. Shimizu, Tetrahedron Lett. 2001, 42, 5473-5476.
9. [4a] E. Erdik, Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Chichester, 1995, pp. 41-52.
10. [4b] E. Erdik, T. Daskapan, Synth. Commun. 1999, 29, 3989-3997.
11. [4c] E. Erdik, T. Daskapan, J. Chem. Soc., Perkin Trans. 1 1999, 3139-3142.
12. [4d] E. Erdik, T. Daskapan, Tetrahedron Lett. 2002, 43, 6237-6239.
13. [5a] J. Vidal, J. Drouin, A. Collet, J. Chem. Soc., Chem. Commun. 1991, 435-437.
14. [5b] J. Vidal, L. Guy, S. Stérin, A. Collet, J. Org. Chem. 1993, 58, 4791-4793.
15. [5c] J. Vidal, S. Damestoy, A. Collet, Tetrahedron Lett. 1995, 36, 1439-1442.
16. [5d] J. Vidal, S. Damestoy, L. Guy, J. C. Hannachi, A. Aubry, A. Collet, Chem. Eur. J. 1997, 3, 1691-1709.
17. [5e] J. Vidal, J. C. Hannachi, G. Hourdin, J. C. Mulatier, A. Collet, Tetrahedron Lett. 1998, 39, 8845-8848.
18. [5f] D. A. Niederer, J. T. Kapron, J. C. Vederas, Tetrahedron Lett. 1993, 34, 6859-6862.
19. [5g] A. Armstrong, M. Athin, S. Swallow, Tetrahedron Lett. 2000, 41, 2247-2251.
20. [6a] J. P. Genet, J. Hajicek, L. Bischoff, C. Greck, Tetrahedron Lett. 1992, 33, 2677-2680.
21. [6b] J. P. Genet, C. Greck, Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Chichester, 1995, pp. 898-899.
22. [6c] C. Greck, L. Bischoff, F. Ferreira, J. P. Genet, J. Org. Chem. 1995, 60, 7010-7012.
23. [7a] A. Casarini, P. Dembech, D. Lazzari, E. Marini, G. Reginato, A. Ricci, G. Seconi, J. Org. Chem. 1993, 58, 5620-5623.
24. [7b] P. Bernardi, P. Dembech, G. Fabbri, A. Ricci, G. Seconi, J. Org. Chem. 1999, 64, 641-643.
25. R. Lenarsic, M. Kocevar, S. Polanc, J. Org. Chem. 1999, 64, 2558-2563.
26. For chiral organometallic reagents, see: [9a] D. K. An, K. Hirakawa, S. Okamoto, F. Sato, Tetrahedron Lett. 1999, 40, 3737-3740.
27. [9b] R. W. Hoffmann, B. Hölzer, O. Knopff, Org. Lett. 2001, 3, 1945-1948.
28. For chiral phosphorous stabilized anions, see: [10a] S. E. Denmark, N. Chatani, S. V. Pansare, Tetrahedron 1992, 48, 2191-2208.
29. [10b] G. Jommi, G. Miglierini, R. Pagliarin, G. Sello, M. Sisti, Tetrahedron 1992, 48, 7275-7288.
30. [10c] S. Hanessian, Y. L. Bennani, Synthesis 1994, 1272-1274.
31. [10d] R. Pagliarin, G. Papeo, G. Sello, M. Sisti, L. Paleari, Tetrahedron 1996, 52, 13783-13794.
32. W. Oppolzer, O. Tamura, G. Sundarababu, M. Signer, J. Am. Chem. Soc. 1992, 114, 5900-5902.
33. G. V. Shustov, G. K. Kadorkina, S. V. Varlamov, A. V. Kachanov, R. G. Kostyanovsky, A. Rauk, J. Am. Chem. Soc. 1992, 114, 1616-1623.
34. A. Armstrong, M. Athin, S. Swallow, Tetrahedron: Asymmetry 2001, 12, 535-538.
35. P. C. B. Page, C. Limousin, V. L. Murrell, J. Org. Chem. 2002, 67, 7787-7796.
36. [15a] J. M. Harris, E. A. Bolessa, A. J. Mendonca, S. C. Feng, J. C. Vederas, J. Chem. Soc., Perkin Trans. 1 1995, 1945-1950.
37. [15b] J. M. Harris, E. A. Bolessa, J. C. Vederas, J. Chem. Soc., Perkin Trans. 1 1995, 1951-1959.
38. J. M. Harris, R. McDonald, J. C. Vederas, J. Chem. Soc., Perkin Trans. 1 1996, 2669-2674.
39. D. A. Evans, S. G. Nelson, J. Am. Chem. Soc. 1997, 119, 6452-6453.
40. [18a] D. A. Evans, D. S. Johnson, Org. Lett. 1999, 1, 595-598.
41. [18b] K. Juhl, K. A. Jorgensen, J. Am. Chem. Soc. 2002, 124, 2420-2421.
42. Y. Yamashita, H. Ishitani, S. Kobayashi, Can. J. Chem. 2000, 78, 666-672.
43. [20a] B. List, J. Am. Chem. Soc. 2002, 124, 5656-5657.
44. [20b] A. Bogevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jorgensen, Angew. Chem. 2002, 114, 1868-1871; Angew. Chem. Int. Ed. 2002, 41, 1790-1793.
45. [20b] A. Bogevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jorgensen, Angew. Chem. 2002, 114, 1868-1871; Angew. Chem. Int. Ed. 2002, 41, 1790-1793.
46. [20c] N. Kumaragurubaran, K. Juhl, A. Bogevig, K. A. Jorgensen, J. Am. Chem. Soc 2002, 124, 6254-6255.
47. [20d] R. O. Duthaler, Angew. Chem. 2003, 115, 1005-1008; Angew. Chem. Int. Ed. 2003, 42, 975-978.
48. [20d] R. O. Duthaler, Angew. Chem. 2003, 115, 1005-1008; Angew. Chem. Int. Ed. 2003, 42, 975-978.
49. W. Lwowski, J. M. Maricich, J. Am. Chem. Soc. 1965, 87, 3630-3637.
50. [22a] S. Fioravanti, M. A. Loreto, L. Pellacani, P. A. Tardella, J. Org. Chem. 1985, 50, 5365-5368.
51. [22b] S. Fioravanti, M. A. Loreto, L. Pellacani, P. A. Tardella, J. Chem. Res. (S) 1987, 310-311.
52. S. Fioravanti, M. A. Loreto, L. Pellacani, P. A. Tardella, Tetrahedron 1991, 47, 5877-5882.
53. E. Felice, S. Fioravanti, L. Pellacani, P. A. Tardella, Tetrahedron Lett. 1999, 40, 4413-4416.
54. D. Enders, C. Poiesz, R. Joseph, Tetrahedron: Asymmetry 1998, 9, 3709-3716.
55. [26a] P. C. B. Page, S. M. Allin, E. W. Collington, R. A. E. Carr, Tetrahedron Lett. 1994, 35, 2427-2430.
56. [26b] P. C. B. Page, M. J. McKenzie, S. M. Allin, D. R. Buckle, Tetrahedron 2000, 56, 9683-9685.
57. [27a] O. Diels, H. Behncke, Ber. 1924, 57, 653-656.
58. [27b] Di-tertbutyl azodicarboxylate: M. Klinge, J. C. Vederas, Encyclopedia of Reagentsfor Organic Synthesis, John Wiley & Sons, Chichester, 1995, pp. 1586-1591.
59. [27c] Dibenzyl azodicarboxylate: Y. Leblanc, Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Chichester, 1995, pp. 1532-1533.
60. [28a] W. Oppolzer, R. Moretti, Helv. Chim. Acta 1986, 69, 1923-1926.
61. [28b] W. Oppolzer, R. Moretti, Tetrahedron 1988, 44, 5541-5552.
62. C. Gennari, G. Bertolini, L. Colombo, J. Am. Chem. Soc. 1986, 108, 6394-6395.
63. [30a] D. A. Evans, T. C. Britton, R. L. Dorow, J. F. Dellaria, J. Am. Chem. Soc. 1986, 108, 6395-6397.
64. [30b] D. A. Evans, T. C. Britton, R. L. Dorow, J. F. Dellaria, Tetrahedron 1988, 44, 5525-5540.
65. L. A. Trimble, J. C. Vederas, J. Am. Chem. Soc. 1986, 108, 6397-6399.
66. [32a] P. Arya, R. N. Ben, H. Qin, Tetrahedron Lett. 1998, 39, 6131-6134.
67. [32b] R. N. Ben, A. Orellana, P. Arya, J. Org. Chem. 1998, 63, 4817-4820.
68. D. A. Evans, T. C. Britton, J. A. Ellman, R. L. Dorow, J. Am. Chem. Soc. 1990, 112, 4011-4030.
69. [34a] D. A. Evans, D. A. Evrard, S. D. Rychnovsky, T. Früh, W. G. Whittingham, K. M. De Vries, Tetrahedron Lett. 1992, 33, 1189-1192.
70. [34b] C. Vergne, J. P. Bouillon, J. Chastanet, M. Bois-Choussy, J. Zhu, Tetrahedron: Asymmetry 1998, 9, 3095-3103.
71. W. Oppolzer, O. Tamura, Tetrahedron Lett. 1990, 31, 991-994.
72. N. Zheng, J. D. Armstrong III, J. C. McWilliams, R. P. Volante, Tetrahedron Lett. 1997, 38, 2817-2820.
73. P. W. H. Chan, I. F. Cottrell, M. G. Moloney, Tetrahedron: Asymmetry 1999, 10, 3887-3891.
74. J. L. Vicario, D. Badia, L. Carrillo, E. Anakabe, Tetrahedron: Asymmetry 2002, 13, 745-751.
75. H. Estermann, D. Seebach, Helv. Chim. Acta 1988, 71, 1824-1839.
76. E. Fernandez-Megia, M. M. Paz, F. J. Sardina, J. Org. Chem. 1994, 59, 7643-7652.
77. R. Badorrey, C. Cativiela, M. D. Diaz-de-Villegas, J. A. Galves, Tetrahedron: Asymmetry 1995, 6, 2787-2796.
78. G. Frater, Helv. Chim. Acta 1979, 62, 2825-2828.
79. J. Zimmermann, D. Seebach, Helv. Chim. Acta 1988, 1143-1155.
80. [44a] J. P. Genet, S. Jugė, S. Mallart, Tetrahedron Lett. 1988, 29, 6765-6768.
81. [44b] G. Guanti, L. Banfi, E. Narisano, Tetrahedron 1988, 44, 5553-5562.
82. A. R. Sting, D. Seebach, Tetrahedron 1996, 52, 279-290.
83. [46a] G. Guanti, L. Banfi, E. Narisano, Tetrahedron Lett. 1989, 30, 5511-5514.
84. [46b] G. Guanti, L. Banfi, E. Narisano, S. Thea, Synlett 1992, 311-312.
85. [46c] G. Guanti, L. Banfi, E. Narisano, R. Riva, Tetrahedron Lett. 1992, 33, 2221-2222.
86. [46d] L. Banfi, G. Cascio, G. Guanti, E. Manghisi, E. Narisano, R. Riva, Tetrahedron 1994, 50, 11967-11982.
87. [46e] G. Guanti, L. Banfi, E. Narisano, Tetrahedron Lett. 1989, 30, 5507-5510.
88. C. Greck, L. Bischoff, F. Ferreira, C. Pinel, E. Piveteau, J. P. Genet, Synlett 1993, 475-477.
89. [48a] R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, J. Am. Chem. Soc. 1987, 109, 5856-5858.
90. [48b] J. P. Genet, C. Pinel, V. Ratovelomanana-Vidal, S. Mallart, X. Pfister, M. C. Caño de Andrade, J. A. Lafitte, Tetrahedron: Asymmetry 1994, 5, 665-674.
91. [48c] J. P. Genet, C. Pinel, V. Ratovelomanana-Vidal, S. Mallart, X. Pfister, L. Bischoff, M. C. Caño de Andrade, S. Darses, C. Galopin, J. A. Lafitte, Tetrahedron: Asymmetry 1994, 5, 675-690.
92. [48d] J. P. Genet, C. Pinel, V. Ratovelomanana-Vidal, M. C. Caño de Andrade, X. Pfister, P. Guerreiro, J. Y. Lenoir, Tetrahedron Lett. 1995, 36, 4801-4804.
93. [48e] V. Ratovelomanana-Vidal, J. P. Genet, J. Organomet. Chem. 1998, 567, 163-171.
94. [49a] A. Girard, C. Greck, J. P. Genet, Tetrahedron Lett. 1998, 39, 4259-4263.
95. [49b] O. Poupardin, F. Ferreira, C. Greck, J. P. Genet, Tetrahedron Lett. 2001, 42, 1523-1526.
96. O. Labeeuw, P. Phansavath, J. P. Genet, Tetrahedron Lett. 2003, 44, 6383-6386.
97. C. Greck, O. Poupardin, Targets in Heterocyclic Systems 2002, 6, 312-324.
98. [52a] C. Greck, L. Bischoff, J. P. Genet, Tetrahedron: Asymmetry 1995, 6, 1989-1994.
99. [52b] C. Greck, F. Ferreira, J. P. Genet, Tetrahedron Lett. 1996, 37, 2031-2034.
100. [52c] F. Ferreira, C. Greck, J. P. Genet, Bull. Soc. Chim. Fr. 1997, 134, 615-621.
101. [52d] O. Poupardin, C. Greck, J. P. Genet, Synlett 1998, 1279-1281.
102. [52e] O. Poupardin, C. Greck, J. P. Genet, Tetrahedron Lett. 2000, 41, 8795-8797.
103. B. Drouillat, O. Poupardin, Y. Bourdreux, C. Greck, Tetrahedron Lett. 2003, 44, 2781-2783.