Enantioselective copper-catalysed conjugate addition

European Journal of Organic Chemistry

Volumn , Issue 19, 2002, Pages 3221-3236

  Alexakis, Alexandre ^a   Benhaim, Cyril ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Asymmetric catalysis; Copper; Michael additions; P ligands; S ligands

Indexed keywords

COPPER; ORGANOMETALLIC COMPOUND;

CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CONJUGATE; ENANTIOMER; ENANTIOSELECTIVITY; ORGANIC CHEMISTRY; SHORT SURVEY;

EID: 0036793999     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200210)2002:19<3221::AID-EJOC3221>3.0.CO;2-U     Document Type: Short Survey

References (127)

1. [1a] P. Perlmutter, Conjugate Addition Reaction in Organic Synthesis, Tetrahedron Organic Chemistry Series, no. 9, Pergamon Press, Oxford, 1992.
2. [1b] Y. Yamamoto, Methods Org. Chem. (Houben-Weyl), 1995, vol. 4 ("Stereoselective Synthesis"), pp. 2041-2057.
3. [2a] J. A. Kozlowski, in: Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Oxford, Pergamon Press, 1991, vol. 4, pp. 169-198.
4. [2b] R. J. K. Taylor, Synthesis 1985, 364-392.
5. [2c] G. H. Posner, Org. React. 1974, 22, 253-400.
6. [2d] G. H. Posner, Org. React. 1972, 19, 1-113.
7. [2e] B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631.
8. [3a] B. E. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 77.
9. [3b] A. Alexakis, in: Organocopper Reagents, a Practical Approach (Ed.: R. J. K. Taylor), Chapt. 8. Oxford: Oxford University Press, 1994, pp. 159-83.
10. [3c] R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
11. [3d] I. Ojima, Catalytic Asymmetric Synthesis, Weinheim, VCH, 1993.
12. [3e] N. Krause, A. Gerold, Angew. Chem. Int. Ed. Engl. 1997, 36, 186-204.
13. [4a] A. Alexakis, in: Transition Metal Catalysed Reactions (Eds.: S.-I. Murahashi, S. G. Davies), IUPAC Blackwell Science, Oxford, 1999, p. 303.
14. [4b] K. Tomioka, Y. Nagaoka, in: Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 2000, p. 1105.
15. [4c] M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033.
16. [4d] N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171.
17. M. S. Karash, P. O. Tawney, J. Am. Chem. Soc. 1941, 63, 2308.
18. A. Alexakis, J. Frutos, P. Mangeney, Tetrahedron: Asymmetry 1993, 4, 2427-2430.
19. A. Alexakis, S. Mutti, J. F. Normant, J. Am. Chem. Soc. 1991, 113, 6332-6334.
20. C. K. Reddy, A. Devasagayaraj, P. Knochel, Tetrahedron Lett. 1996, 37, 4495-4498.
21. A. E. Greene, J. P. Lansard, J. L. Luche, C. Petrier, J. Org. Chem. 1984, 49, 931-932.
22. [10a] T. Kauffmann, G. Hopp, B. Laarmann, D. Stegemann, D. Wingbermühle, Tetrahedron Lett. 1990, 31, 511-514.
23. [10b] A. H. de Vries, B. L. Feringa, Tetrahedron: Asymmetry 1997, 8, 1377-1378.
24. [11a] E. Nakamura, S. Aoki, K. Sekiya, H. Oshino, I. Kuwajima, J. Am. Chem. Soc. 1987, 109, 8056-8066.
25. [11b] M. Kitamura, T. Miki, K. Nakano, R. Noyori, Bull. Chem. Soc. Jpn. 2000, 73, 999-1014.
26. [11c] M. Kitamura, T. Miki, K. Nakano, R. Noyori, Tetrahedron Lett. 1996, 37, 5141-5144.
27. [12a] K. Soai, T. Hayasaka, S. Ugajin, S. Yokoyama, Chem. Lett. 1988, 1571.
28. [12b] C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205-1215.
29. [12c] A. H. M. de Vries, J. F. G. A. Jansen, B. L. Feringa, Tetrahedron 1994, 50, 4479-4491.
30. [12d] P.-E. Tong, P. Li, A. S. C. Chan, Tetrahedron. Asymmetry 2001, 12, 2301-2304.
31. E. Nakamura, S. Mori, Angew. Chem. Int. Ed. 2000, 39, 3750-3771.
32. [14a] M. P. Bertrand, L. Feray, R. Nouguier, P. Perfetti, J. Org. Chem. 1999, 64, 9189.
33. [14b] H. Van der Deen, R. M. Kellogg, B. L. Feringa, Org. Lett. 2000, 2, 1593-1595.
34. A. Alexakis, J. Burton, J. Vastra, C. Benhaim, X. Fournioux, A. Van den Heuvel, J.-M. Leveque, F. Maze, S. Rosset, Eur. J. Org. Chem. 2000, 4011-4027.
35. A. Alexakis, J. Vastra, P. Mangeney, Tetrahedron Lett. 1997, 38, 7745-7748.
36. A. Alexakis, C. Benhaim, S. Rosset, M. Humam, J. Am. Chem. Soc, 2002, 124, 5262.
37. A. Alexakis, J. Burton, J. Vastra, P. Mangeney, Tetrahedron: Asymmetry 1997, 8, 3987-3990.
38. F.-Y. Zhang, A. S. C. Chan, Tetrahedron: Asymmetry 1998, 9, 1179-1182.
39. T. Morimoto, Y. Yamaguchi, M. Suzuki, A. Saitoh, Tetrahedron Lett. 2000, 41, 10025-10029.
40. [21a] S. J. Degrado, H. Mizutani, A. H. Hoveyda, J. Am. Chem. Soc 2001, 123, 755-756.
41. [21b] H. Mizutani, S. J. Degrado, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 779-781.
42. [22a] I. Chataigner, C. Gennari, S. Ongeri, U. Piarulli, S. Ceccarelli, Chem. Eur. J. 2001, 7, 2628-2634.
43. [22b] S. Ongeri, U. Piarulli, R. F. W. Jackson, C. Gennari, Eur. J. Org. Chem. 2001, 803-807.
44. [23a] Y. Takemoto, S. Kuraoka, N. Hamaue, K. Aoe, H. Hiramatsu, C. Iwata, Tetrahedron 1996, 52, 14177-14188.
45. [23b] Y. Takemoto, S. Kuraoka, N. Hamaue, C. Iwata, Tetrahedron: Asymmetry 1996, 7, 993-996.
46. [24a] X. Hu, H. Chen, X. Zhang, Angew. Chem. Int. Ed. 1999, 38, 3518-3521.
47. [24b] X. Hu, H. Chen, X. Zhang, Acta Chim. Sin. 2000, 58, 1163-1167.
48. A. H. M. de Vries, A. Meetsma, B. L. Feringa, Angew. Chem. Int. Ed. Engl. 1996, 35, 2374-2376.
49. Y. Vastra, Ph.D. thesis, Univ. Pierre et Marie Curie, Paris, 1998.
50. [27a] E. Keller, J. Maurer, R. Naasz, T. Schader, A. Meetsma, B. L. Feringa, Tetrahedron: Asymmetry 1998, 9, 2409-2413.
51. [27b] G. Delapierre, T. Constantieux, J. M. Brunel, G. Buono, Eur. J. Org. Chem. 2000, 2507-2511.
52. Q.-L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467-4478.
53. L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. De Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865-2878.
54. S. M. W. Bennett, S. M. Brown, A. Cunningham, M. R. Dennis, J. P. Muxworthy, M. A. Oakley, S. Woodward, Tetrahedron 2000, 56, 2847-2855.
55. Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988-2989.
56. A. Alexakis, C. Benhaim, Org. Lett. 2000, 2, 2579-2581.
57. A. Martorell, R. Naasz, B. L. Feringa, P. G. Pringle, Tetrahedron: Asymmetry 2001, 12, 2497-2499.
58. T. Mori, K. Kosaka, Y. Nakagawa, Y. Nagaoka, K. Tomioka, Tetrahedron: Asymmetry 1998, 9, 3175-3178.
59. [35a] M. T. Reetz, Pure Appl. Chem. 1999, 71, 1503-1509.
60. [35b] M. T. Reetz, A. Gosberg, D. Moulin, Tetrahedron Lett. 2002, 43, 1189-1191.
61. A. Alexakis, J. Vastra, J. Burton, P. Mangeney, Tetrahedron: Asymmetry 1997, 8, 3193-3196.
62. A. Alexakis, J. Vastra, J. Burton, C. Benhaim, P. Mangeney, Tetrahedron Lett. 1998, 39, 7869-7872.
63. A. Alexakis, C. Benhaim, Tetrahedron: Asymmetry 2001, 12, 1151-1157.
64. A. Mandoli, L. A. Arnold, A. H. M. de Vries, P. Salvadori, B. L. Feringa, Tetrahedron: Asymmetry 2001, 12, 1929-1937.
65. B. L. Feringa, Acc. Chem. Res. 2000, 33, 346-353.
66. A. Alexakis, C. Benhaim, X. Fournioux, A. Van den Heuvel, J.-M. Leveque, S. March, S. Rosset, Synlett 1999, 1811-1813.
67. [42a] A. K. H. Knoebel, I. H. Escher, A. Pfaltz, Synlett 1997, 1429-1431.
68. [42b] I. H. Escher, A. Pfaltz, Tetrahedron 2000, 56, 2879-2888.
69. [42c] I. H. Escher, Ph.D. thesis, Univ. Basel, 2000.
70. O. Huttenloch, J. Spieler, H. Waldmann, Chem. Eur. J. 2001, 7, 671-675.
71. [44a] M. Yan, L.-W. Yang, K.-Y. Wong, A. S. C. Chan, Chem. Commun. 1999, 11-12.
72. [44b] M. Yan, A. S. C. Chan, Tetrahedron Lett. 1999, 40, 6645-6648.
73. [44c] M. Yan, Z.-Y. Zhou, A. S. C. Chan, Chem. Commun. 2000, 115-116.
74. [45a] O. Pamies, M. Dieguez, G. Net, A. Ruiz, C. Claver, Tetrahedron: Asymmetry 2000, 11, 4377-4383.
75. [45b] M. Dieguez, A. Ruiz, C. Claver, Tetrahedron: Asymmetry 2001, 12, 2895-2900.
76. [46a] M. Dieguez, S. Deerenberg, O. Pamies, C. Claver, P. W. N. M. van Leeuwen, P. Kamer, Tetrahedron: Asymmetry 2000, 11, 3161-3166.
77. [46b] M. Dieguez, A. Ruiz, C. Claver, Tetrahedron: Asymmetry 2001, 12, 2861-2866.
78. A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen, C. Benhaim, Synlett 2001, 1375-1378.
79. G. Delapierre, J. M. Brunel, T. Constantieux, G. Buono, Tetrahedron: Asymmetry 2001, 12, 1345-1352.
80. C. Darcel, E. B. Kaloun, R. Merdes, D. Moulin, N. Riegel, S. Thorimbert, J. P. Genet, S. Juge, J. Organomet. Chem. 2001, 624, 333-343.
81. I. Chataigner, C. Gennari, U. Piarulli, S. Ceccarelli, Angew. Chem. Int. Ed. 2000, 39, 916-918.
82. V. Wendisch, N. Sewald, Tetrahedron: Asymmetry 1997, 8, 1253-1257.
83. Y. Nakagawa, K. Matsumoto, K. Tomioka, Tetrahedron: 2000, 56, 2857-2863.
84. P. K. Fraser, S. Woodward, Tetrahedron Lett. 2001, 42, 2747-2749.
85. [54a] F. Guillen, C. L. Winn, A. Alexakis, Tetrahedron: Asymmetry 2001, 12, 2083-2086.
86. [54b] J. Pytkowicz, S. Roland, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 2087-2089.
87. [55a] S. M. W. Bennett, S. M. Brown, J. P. Muxworthy, S. Woodward, Tetrahedron Lett. 1999, 40, 1767-1770.
88. [55b] C. Borner, M. R. Dennis, E. Sinn, S. Woodward, Eur. J. Org. Chem. 2001, 2435-2446.
89. [55c] S. M. W. Bennett, S. M. Brown, A. Cunningham, M. R. Dennis, J. P. Muxworthy, M. A. Oakley, S. Woodward, Tetrahedron 2000, 56, 2847-2855.
90. O. Pamies, G. Net, A. Ruiz, C. Claver, S. Woodward, Tetrahedron: Asymmetry 2000, 11, 871-877.
91. A. H. M. De Vries, R. P. Hof, D. Staal, R. M. Kellogg, B. L. Feringa, Tetrahedron: Asymmetry 1997, 8, 1539-1543.
92. [58a] M. Schinnerl, M. Seitz, A. Kaiser, O. Reiser, Org. Lett. 2001, 3, 4259-4262.
93. [58b] M. Schinnerl, M. Seitz, A. Kaiser, O. Reiser, Org. Lett. 2002, 4, 471.
94. R. B. C. Jagt, R. Imbos, R. Naasz, A. J. Minnaard, B. L. Feringa, Isr. J. Chem. 2001, 41, 221-229.
95. R. Imbos, M. H. G. Brilman, M. Pineschi, B. L. Feringa, Org. Lett. 1999, 1, 623-625.
96. R. Naasz, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Angew. Chem. Int. Ed. 2001, 40, 930.
97. N. Sewald, V. Wendisch, Tetrahedron: Asymmetry 1998, 9, 1341-1344.
98. P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188.
99. [64a] R. Naasz, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Chem. Commun. 2001, 735-736.
100. [64b] R. Naasz, L. A. Arnold, M. Pineschi, E. Keller, B. L. Feringa, J. Am. Chem. Soc. 1999, 121, 1104-1105.
101. [65a] B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos, A. H. M. De Vries, Angew. Chem. Int. Ed. Engl. 1997, 36, 2620-2623.
102. [65b] L. A. Arnold, R. Naasz, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2001, 123, 5841-5842.
103. A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358-4359.
104. C. Borner, P. J. Goldsmith, S. Woodward, J. Gimeno, S. Gladiali, D. Ramazzotti, Chem. Commun. 2000, 2433-2434.
105. S. M. W. Bennett, S. M. Brown, G. Conole, M. R. Dennis, P. K. Fraser, S. Radojevic, M. McPartlin, C. M. Topping, S. Woodward, J. Chem. Soc., Perkin Trans. 1 1999, 3127-3132.
106. [69a] G. M. Villacorta, C. P. Rao, S. J. Lippard, J. Am. Chem. Soc. 1988, 110, 3175-3182.
107. [69b] K. H. Ahn, R. B. Klassen, S. J. Lippard, Organomet. 1990, 9, 3178-3181.
108. [70a] F. Lambert, D. M. Knotter, M. D. Janssen, M. van Klaveren, J. Boersma, G. van Koten, Tetrahedron: Asymmetry 1991, 2, 1097-1100.
109. [70b] D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Speck, G. van Koten, J. Am. Chem. Soc. 1992, 114, 3400-3410.
110. [71a] Q. L. Zhou, A. Pfaltz, Tetrahedron Lett. 1993, 34, 7725-7728.
111. [71b] Q. L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467-4479.
112. M. Spescha, G. Rihs, Helv. Chim. Acta 1993, 76, 1219-1230.
113. D. Seebach, G. Jaeschke, A. Pichota, L. Audergon, Helv. Chim. Acta 1997, 80, 2515.
114. E. L. Stangeland, T. Sammakia, Tetrahedron 1997, 53, 16503-16510.
115. M. T. Reetz, A. Kindler, J. Organomet. Chem. 1995, 502, C5-C7.
116. [76a] M. Kanai, Y. Nakagawa, K. Tomioka, Tetrahedron 1999, 55, 3843-3854.
117. [76b] M. Kanai, K. Tomioka, Tetrahedron Lett. 1995, 36, 4275-4278 and references cited therein.
118. C. Benhaim, Ph.D. thesis, Univ. Geneva, 2002.
119. T. C. Kinahan, H. Tye, Tetrahedron: Asymmetry 2001, 12, 1255-1257.
120. C. G. Arena, G. Calabro, G. Francio, G. Faraone, Tetrahedron: Asymmetry 2000, 11, 2387-2391.
121. P. Muller, P. Nury, G. Bernardinelli, Helv. Chim. Acta 2000, 83, 843-854.
122. J. P. G. Versleijen, A. M. Van Leusen, B. L. Feringa, Tetrahedron Lett. 1999, 40, 5803-5806.
123. [82a] C. Benhaim, P. Meier, P. Kundig, A. Alexakis, unpublished results.
124. [82b] C. Benhaim, A. Tomassini, A. Alexakis, unpublished results.
125. [82c] C. Benhaim, C. Bothua, P. Kundig, A. Alexakis, unpublished results.
126. [82d] S. Rosset, J. Allamand, C. Benhaim, A. Alexakis, unpublished results.
127. P. K. Fraser, S. Woodward, personal communication.