Organocatalytic asymmetric aza-Michael additions

Chemistry - A European Journal

Volumn 15, Issue 42, 2009, Pages 11058-11076

  Enders, Dieter ^a   Wang, Chuan ^a   Liebich, Jens X ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric synthesis; Br nsted catalysis; Domino reactions; Michael addition; Organocatalysis

Indexed keywords

ASYMMETRIC SYNTHESIS; AZA-MICHAEL ADDITION; AZA-MICHAEL REACTION; CONJUGATE ADDITION; DOMINO REACTIONS; MICHAEL ACCEPTORS; MICHAEL ADDITION; NITROGEN NUCLEOPHILES; ORGANOCATALYSIS; ORGANOCATALYTIC; SYNTHETIC ORGANIC CHEMISTRY;

AMIDES; AMINES; AMINO ACIDS; CATALYSIS; ELECTRON TRANSITIONS; ORGANIC ACIDS; RATE CONSTANTS; REACTION KINETICS;

ADDITION REACTIONS;

EID: 70350506798     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902236     Document Type: Review

References (139)

1. a) T. Purdie, Ber. Dtsch. Chem. Ges. 1881, 14, 2238-2286;
2. b) A. Hantzsch, Justus Liebigs Ann. Chem. 1882, 215, 1-82;
3. c)T. Komnenos, Justus Liebigs Ann. Chem. 1883, 218, 145-169;
4. d) L. Claisen, Justus Liebigs Ann. Chem. 1883, 218, 121-129;
5. e) L. Claisen, L. Crismer, Justus Liebigs Ann. Chem. 1883, 218, 129-144;
6. f) L. Claisen, J. Prakt. Chem. 1886, 35, 413-415.
7. A. Michael, J. Prakt. Chem. 1886, 35, 349.
8. P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
9. Reviews: intramolecular Michael additions: a) R. D. Little, M. R. Masjedizadeh, O. Wallquist, J. I. Mcloughlin, Org. React. 1995, 47, 315-552; oxa-Michael additions:
10. b) A. Berkessel in Methods of Organic Chemistry (Houben-Weyl), Vol.E21e (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, pp. 4818-4856;
11. c) M. Schäfer, K. Drauz, M. Schwärm in Methods of Organic Chemistry (Houben-Weyl), Vol.E21e (Eds.: G. Helmchen, J. Mulzer, R. W. Hoffmann, E. Schaumann), Thieme, Stuttgart, 1995, pp. 5588-5642; enantioselective Michael additions:
12. d) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; catalytic Michael additions:
13. e)N. Krause, A. Hoffmann-Röder, Synthesis 2001, 01710196;
14. g) J. Christoffers, G. Koripelly, A. Rosiak, M. Rössle, Synthesis 2007, 1279-1300; phospha-Michael additions:
15. f) D. Enders, A. Saint-Dizier, M. I. Lannou, A. Lenzen, Eur. J. Org. Chem. 2006, 2949; sulpha-Michael additions:
16. h) D. Enders, K. Luttgen, A. A. Narine, Synthesis 2007, 959-980.
17. F. Loydl, Justus Liebigs Ann. Chem. 1878, 192, 80-89.
18. a) N. Sokoloff, P. Latschinoff, Ber. Dtsch. Chem. Ges. 1874, 7, 1384-1387;
19. b)W. Heintz, N. Sokoloff, P. Latschinoff, Ber. Dtsch. Chem. Ges. 1874, 7, 1518-1520;
20. c) P. R. Haeseler, Org. Synth. 1926, 6, 28-30.
21. E. Juaristi, Enantioselective Synthesis of ß-Amino Acids, WileyVCH, Weinheim, 1997.
22. a) G. I. Georg, The Organic Chemistry of ß-Lactams, Wiley-VCH, Weinheim, 1993;
23. b) P. A. Magriotis, Angew. Chem. 2001, 113, 4507-4509;
24. Angew. Chem. Int. Ed. 2001, 40, 4377-4379.
25. For auxiliary and chiral starting material based reactions, see: a) D. Enders, W. Bettray, G. Raabe, J. Runsink, Synthesis 1994, 1322-1326;
26. b) D. Enders, H. Wahl, W. Bettray, Angew. Chem. 1995, 107, 527-529;
27. Angew. Chem. Int. Ed. Engl. 1995, 34, 455-457;
28. c) D. Enders, J. Wiedemann, W. Bettray, Synlett 1995, 369-371;
29. d) D. Enders, J. Wiedemann, Synthesis 1996, 1443-1450;
30. e) D. Enders, J. Wiedemann, Liebigs Ann. 1997, 699-706;
31. f) D. Enders, S. F. Müller, G. Raabe, Angew. Chem. 1999, 111, 212-214;
32. Angew. Chem. Int. Ed. 1999, 38, 1195-1197;
33. g) D. Enders, S. E. Muller, G. Raabe, Angew. Chem. 1999, 111, 212-214;
34. Angew. Chem. Int. Ed. 1999, 38, 195-197;
35. h)D. Enders, S. F. Muller, G. Raabe, J. Runsink, Eur. J. Org. Chem. 2000, 879-892;
36. i) G. Cardillo, L. Gentilucci, V. De Matteis, J. Org. Chem. 2002, 67, 5957-5962;
37. j) D. Enders, S. Wallert, Synlett 2002, 0304-0306;
38. k) M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035;
39. l) A. G. Moglioni, E. Muray, J. A. Castillo, A. AlvarezLarena, G. Y. Moltrasio, V. Branchadell, R. M. Ortuno, J. Org. Chem. 2002, 67, 2402-2410;
40. m) G. V. M. Sharma, V. G. Reddy, A. S. Chander, K. R. Reddy, Tetrahedron: Asymmetry 2002, 13, 21-24;
41. n)D. Enders, S. Wallert, J. Runsink, Synthesis 2003, 1856-1868;
42. o) M. Sani, L. Bruche, G. Chiva, S. Fustero, J. Piera, A. Volonterio, M. Zanda, Angew. Chem. 2003, 115, 2106-2109;
43. Angew. Chem. Int. Ed. 2003, 42, 2060-2063;
44. p) J. Etxebarria, J. L. Vicario, D. Badia, L. Carrillo, J. Org. Chem. 2004, 69, 2588-2590;
45. q) S. G. Davies, A. D. Smith, P.D. Price, Tetrahedron: Asymmetry 2005, 16, 2833-2891;
46. r) J. Turconi, L. Lebeau, J.-M. Paris, C. Mioskowski, Tetrahedron 2006, 62, 8109-8114;
47. s) M. Koutsaplis, P. C. Andrews, S. D. Bull, P. J. Duggan, B. H. Fraser, P. Jensen, Chem. Commun. 2007, 3580-3582;
48. t) L.-J. Chen, D.-R. Hou, Tetrahedron: Asymmetry 2008, 19, 715-720;
49. u) G. Pandey, M. Balakrishnan, P. S. Swaroop, Eur. J. Org. Chem. 2008, 5839-5847;
50. v) S. Fustero, G. Chiva, J. Piera, J. F. SanzCervera, A. Volonterio, M. Zanda, C. R. de Arellano, J. Org. Chem. 2009, 74, 3122-3132.
51. L. Falborg, K. A. Jørgensen, J. Chem. Soc. Perkin Trans. 1 1996, 2823-2826.
52. For recent selected examples of metal catalyzed reactions, see: a) P. H. Phua, J. G. de Vries, K. K. Hii, Adv. Synth. Catal. 2005, 347, 1775-1780;
53. b) J. L. Vicario, D. Badia, L. Carrillo, J. Etxebarria, E. Reyes, N. Ruiz, Org. Prep. Proced. Int. 2005, 37, 513-538;
54. c) L.-W. Xu, C.-G. Xia, Eur. J. Org. Chem. 2005, 633-639;
55. d) S. Kikuchi, H. Sato, S.-i. Fukuzawa, Synlett 2006, 1023-1026;
56. e) P. H. Phua, A. J. P. White, J. G. de Vries, King K. Hii, Adv. Synth. Catal. 2006, 348, 587-592;
57. f) M. P. Sibi, T. Soeta, J. Am. Chem. Soc. 2007, 129, 4522-4523;
58. g) I. Reboule, R. Gil, J. Collin, Eur. J. Org. Chem. 2008, 532-539;
59. h) S. H. Kang, Y. K. Kang, D. Y Kim, Tetrahedron 2009, 65, 5676-5679.
60. For recent reviews on organocatalysis, see: a) A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005;
61. b) P. I. Dalko, Enantioselective Organocatalysis: Reactions and Experimental Procedures, Wiley-VCH, Weinheim, 2007;
62. c) H. Pellissier, Tetrahedron 2007, 63, 9267-9331;
63. d) special issue on organocatalysis: Chem. Rev. 2007, 107, 5413-5883;
64. e) R. M. de Figueiredo, M. Christmann, Eur. J. Org. Chem. 2007, 2575-2600;
65. f) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716-4739;
66. Angew. Chem. Int. Ed. 2008, 47, 4638-4660;
67. g) D. Enders, A.A. Narine, J. Org. Chem. 2008, 73, 7857-7870;
68. h) H. Kotsuki, H. Ikishima, A. Okuyama, Heterocycles 2008, 75, 151-191;
69. i) H. Kotsuki, H. Ikishima, A. Okuyama, Heterocycles 2008, 75, 493-529;
70. j) P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232-6265;
71. Angew. Chem. Int. Ed. 2008, 47, 6138-6171;
72. k)K. A. Jørgensen, S. Bertelsen, Chem. Soc. Rev. 2009, 38, 2178-2189.
73. For recent reviews on organocatalytic 1,4-additions, see: a) A. Alexakis, S. Sulzer-Mossé, Chem. Commun. 2007, 3123-3125;
74. b) D. Almasi, D. A. Alonso, C. Najera, Tetrahedron: Asymmetry 2007, 18, 299-365;
75. c) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716;
76. d) J. L. Vicario, D. Badía, L. Carrillo, Synthesis 2007, 2065-2092.
77. K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 222, 4243-4244.
78. Y. K. Chen, M. Yoshida, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 225, 9328-9329.
79. J. Vesely, I. Ibrahem, R. Rios, G.-L. Zhao, Y. Xu, A. Córdova, Tetrahedron Lett. 2007, 48, 2193-2198.
80. H. Jiang, J. B. Nielsen, M. Nielsen, K. A. Jørgensen, Chem. Eur. J. 2007, 13, 9068-9075.
81. P. Diner, M. Nielsen, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 2029-2033;
82. Angew. Chem. Int. Ed. 2007, 46, 1983-1987.
83. U. Uria, J. L. Vicario, D. Badia, L. Carrillo, Chem. Commun. 2007, 2509-2511.
84. Q.-Y Lin, D. Meloni, Y.-C. Pan, M. Xia, J. Rodgers, S. Shepard, M. Li, L. Galya, B. Metcalf, T-Y Yue, P.-L. Liu, J. Zhou, Org. Lett. 2009, 22, 1999-2002.
85. L.-Y Chen, H. He, B.-J. Pei, W.-H. Chan, A. W. M. Lee, Synthesis 2009, 1573-1577.
86. K. Takasu, S. Maiti, M. Ihara, Heterocycles 2003, 59, 51-55.
87. S. Fustero, D. Jimenez, J. Moscardo, S. Catalán, C. del Pozo, Org. Lett. 2007, 9, 5283-5286.
88. E. C. Carlson, L. K. Rathbone, H. Yang, N. D. Collett, R. G. Carter, J. Org. Chem. 2008, 73, 5155-5158.
89. S. Fustero, J. Moscardo, D. Jimenez, M. D. Perez-Carrion, M. Sanchez-Rosello, C. del Pozo, Chem. Eur. J. 2008, 14, 9868-9872.
90. J. Veselý, I. Ibrahem, G.-L. Zhao, R. Rios, A. Cordova, Angew. Chem. 2007, 119, 792-795;
91. Angew. Chem. Int. Ed. 2007, 46, 778781.
92. H. Arai, N. Sugaya, N. Sasaki, K. Makino, S. Lectard, Y. Hamada, Tetrahedron Lett. 2009, 50, 3329-3332.
93. I. Ibrahem, R. Rios, J. Veselý, G.-L. Zhao, A. Cordova, Chem. Commun. 2007, 849-851.
94. H. Sunden, R. Rios, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Cordova, Adv. Synth. Catal. 2007, 349, 827-832.
95. H. Li, J. Wang, H.-X. Xie, L.-S. Zu, W. Jiang, E. N. Duesler, W. Wang, Org. Lett. 2007, 9, 965-968.
96. Y Yoshitomi, H. Arai, K. Makino, Y. Hamada, Tetrahedron 2008, 64, 11568-11579.
97. H. Li, L.-S. Zu, H. X. Xie, J. Wang, W. Wang, Chem. Commun. 2008, 5636-5638.
98. A. I. Gerasyuto, R. P. Hsung, N. Sydorenko, B. Slafer, J. Org. Chem. 2005, 70, 4248-4256.
99. G.-L. Zhao, R. Rios, J. Veselý, L. Eriksson, A. Cordova, Angew. Chem. 2008, 120, 8596-8600;
100. Angew. Chem. Int. Ed. 2008, 47, 8468-8472.
101. B. Tan, Z.-G. Shi, P.-J. Chua, Y-X. Li, G. Zhong, Angew. Chem. 2009, 121, 772-775;
102. Angew. Chem. Int. Ed. 2009, 48, 758-761.
103. D. Enders, C. Wang, Synthesis, In Press.
104. T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301-4304.
105. T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2006, 5, 1533-1535.
106. H. Sunden, I. Ibrahem, L. Eriksson, A. Cordova, Angew. Chem. 2005, 117, 4955-4958;
107. Angew. Chem. Int. Ed. 2005, 44, 4877-4880.
108. H. Yang, R. G. Carter, J. Org. Chem. 2009, 74, 5151-5156.
109. S. Khaliel, M. V. Nandakumar, H. Krautscheid, C. Schneider, Synlett 2008, 2705-2707.
110. Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5962-5963.
111. M. Lu, D. Zhu, Y Lu, Y Hou, B. Tan, G. Zhong, Angew. Chem. 2008, 120, 10341-10345;
112. Angew. Chem. Int. Ed. 2008, 47, 10187-10191.
113. D. Zhu, M. Lu, J. Chua, B. Tan, F. Wang, X. Yang, G. Zhong, Org. Lett. 2008, 10, 4585-4588.
114. M. Rueping, C. Azap, Angew. Chem. 2006, 118, 7996-7999;
115. Angew. Chem. Int. Ed. 2006, 45, 7832-7835.
116. H. Liu, L.-F. Cun, A.-Q. Mi, Y-Z. Jiang, L.-Z. Gong, Org. Lett. 2006, 8, 6023-6026.
117. D. Enders, A. Narine, F. Toulgoat, T. Bisschops, Angew. Chem. 2008, 120, 5744-5748;
118. Angew. Chem. Int. Ed. 2008, 47, 5661-5665.
119. D. Uraguchi, D. Nakashima, T. Ooi, J. Am. Chem. Soc. 2009, 131, 7242-7243.
120. Y. Sohtome, A. Tanatani, Y Hashimoto, K. Nagasawa, Chem. Pharm. Bull. 2004, 52, 477-480.
121. J. Wang, L. Zu, H. Li, H. Xie, W. Wang, Synthesis 2007, 2576-2580.
122. M. P. Sibi, K. Itoh, J. Am. Chem. Soc. 2007, 129, 8064-8065.
123. D. Pettersen, F. Piana, L. Bernardi, F. Fini, M. Fochi, V. Sgarzani, A. Ricci, Tetrahedron Lett. 2007, 48, 7805-7808.
124. J. Wang, H. Li, L. Zu, W. Wang, Org. Lett. 2006, 8, 1391-1394.
125. M. Nielsen, W. Zhuang, K. A. Jørgensen, Tetrahedron 2007, 63, 5849-5854.
126. D. Perdicchia, K. A. Jørgensen, J. Org. Chem. 2007, 72, 3565-3568.
127. A. Scettri, A. Massa, L. Palombi, R. Villano, M. R. Acocella, Tetrahedron: Asymmetry 2008, 19, 2149-2152.
128. X. Lu, L. Deng, Angew. Chem. 2008, 120, 7824-7827;
129. Angew. Chem. Int. Ed. 2008, 47, 7710-7713.
130. F. Pesciaioli, F. De Vincentiis, P. Galzerano, G. Bencivenni, G. Bartoli, A. Mazzanti, P. Melchiorre, Angew. Chem. 2008, 120, 8831-8834;
131. Angew. Chem. Int. Ed. 2008, 47, 8703-8706.
132. G. Luo, S. Zhang, W. Duan, W. Wang, Synthesis 2009, 1564-1572.
133. S. Gogoi, C-G. Zhao, D. Ding, Org. Lett. 2009, 11, 2249-2252.
134. S. Fioravanti, M. G. Mascia, L. Pellacani, P. A. Tardella, Tetrahedron 2004, 60, 8073-8077.
135. M. Bandini, A. Eichholzer, M. Tragni, A. Umani-Ronchi, Angew. Chem. 2008, 120, 3282-3285;
136. Angew. Chem. Int. Ed. 2008, 47, 3238-3241.
137. T. E. Horstmann, D. J. Guerin, S. J. Miller, Angew. Chem. 2000, 112, 3781-3784;
138. Angew. Chem. Int. Ed. 2000, 39, 3635-3638.
139. D. J. Guerin, S. J. Miller, J. Am. Chem. Soc. 2002, 124, 2134-2136.