α,α-diarylprolinol ethers: New tools for functionalization of carbonyl compounds

Chemistry - An Asian Journal

Volumn 3, Issue 6, 2008, Pages 922-948

  Mielgo, Antonia ^a   Palomo, Claudio ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Asymmetric catalysis; Enamine activation; Iminium ion activation; Organocatalysis; Tandem reactions

Indexed keywords

ALDEHYDE; CARBONIC ACID; ETHER; IMINE; WATER;

CATALYSIS; CHEMISTRY; REVIEW;

ALDEHYDES; CARBONIC ACID; CATALYSIS; ETHER, ETHYL; IMINES; WATER;

EID: 51749084445     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700417     Document Type: Review

References (343)

1. Y. Izumi, Angew. Chem. 1971, 83, 956-966;
2. Angew. Chem. Int. Ed. Engl. 1971, 10, 871-881.
3. a) C.-H. Wong, G. Withesides, Enzymes in Organic Chemistry, Pergamon Press, Oxford, 1994;
4. b) K. Drauz, H. Waldmann, Eds. ; Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook; Wiley-VCH, Weinheim, 2002, Vols. 1-3;
5. c)Catalytic Antibodies, (Ed.: E. Keinan), Wiley-VCH, Weinheim, 2005.
6. a) I. Ojima, Ed. ; Catalytic Asymmetric Synthesis, VCH, Weinheim, 1993;
7. b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
8. c) Stereoselective Synthesis (Eds.: G. Helmchen, R.W. Hoffmann, J. Mulzer, E. Schaumann), (Houben-Weyl), Thieme, Stuttgart, 1996;
9. d) Comprehensive Asymmetric Catalysis, Vols. 1-3 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
10. e) Comprehensive Asymmetric Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Suppl. 2; Springer, Berlin, 2004;
11. f) D. J. Ramón, M. Yus, Chem. Rev. 2006, 106, 2126-2208.
12. For general reviews, see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840-3864;
13. Angew. Chem. Int. Ed. 2001, 40, 3726-3748;
14. b) M. Benaglia, A. Puglivi, F. Cozzi, Chem. Rev. 2003, 103, 3401-3440;
15. c) B. List, C. Bolm, Adv. Synth. Catal. 2004, 346, 1021-1022 (thematic issue on Organic Catalysis, nos. 9+10);
16. d) K. N. Houk, B. List, Guest, Acc. Chem. Res. 2004, 37, 487 (thematic issue on Asymmetric Organocatalysis, no. 8);
17. e) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248-5286;
18. Angew. Chem. Int. Ed. 2004, 43, 5138-5175;
19. f) A. Berkessel, H. Gröger, Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis; Wiley-VCH, Weinheim, 2005;
20. g) P. Kočovskỳ, A. V. Malkov, Tetrahedron 2006, 62, 255 (thematic issue on Organocatalysis in Organic Synthesis nos. 2+3).
21. For a recent brief overview on the state of the art, see: h) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719-724.
22. For a recent essay on organocatalysis, see: i) C. F. Barbas III, Angew. Chem. 2008, 120, 44-50;
23. Angew. Chem. Int. Ed. 2008, 47, 42-47.
24. W. Marckwald, Ber. Dtsch. Chem. Ges. 1904, 37, 394-354.
25. For other amine-based catalysts, see: cinchona alcaloids: a) K. Kacprzak, J. Gawronski, Synthesis 2001, 961-998;
26. cupreines and cupreidines: b) T. Marcelli, J. H. Van Maarseven, H. Hiemstra, Angew. Chem. 2006, 118, 7658-7666;
27. Angew. Chem. Int. Ed. 2006, 45, 7496-7504;
28. guanidines: c) T. Ishikawa, T. Isobe, Chem. Eur. J. 2002, 8, 552-557;
29. d) T. Ishikawa, T. Kumamoto, Synthesis 2006, 737-752.
30. For the uncovering of the enamine activation concept in asymmetric catalysis, see: a) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396.
31. For reviews, see: b) B. List, Tetrahedron 2002, 58, 5573-5590;
32. c) B. List, Acc. Chem. Res. 2004, 37, 548-557;
33. d) B. List, Chem. Commun. 2006, 819-824.
34. For the uncovering of the iminium activation concept in asymmetric catalysis, see: a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874-9875.
35. For a review, see: b) G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79-87.
36. For recent reviews on tandem and/or domino reactions, see: a) Domino Reactions in Organic Synthesis (Eds.: L. F. Tietze, G. Brasche, K. M. Gerike), Wiley-VCH, Weinheim, 2006;
37. b) J.-C. Wasilke, S. J. Obreg, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001-1020;
38. c) D. J. Ramón, M. Yus, Angew. Chem. 2005, 117, 1628-1661;
39. Angew. Chem. Int. Ed. 2005, 44, 1602-1634;
40. d) D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590-1601;
41. Angew. Chem. Int. Ed. 2007, 46, 1570-1581;
42. e) Ch. J. Chapman, Ch. G. Frost, Synthesis 2007, 1-21.
43. For a previous review, see: C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042-8046;
44. Angew. Chem. Int. Ed. 2006, 45, 7876-7880.
45. For the first reports on the use of catalysts 1 and 2, see: a) M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804-807;
46. Angew. Chem. Int. Ed. 2005, 44, 794-797;
47. b) J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjærsgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 18296-18304;
48. c) Y. Hayashi, H. Gotoh, T. Hayasi, M. Shoji, Angew. Chem. 2005, 117, 4284-4287;
49. Angew. Chem. Int. Ed. 2005, 44, 4212-4215.
50. For reviews on Mannich reactions, see: a) A. Ting, S. E. Schaus Eur. J. Org. Chem. 2007, 5797-5815;
51. b) M. M. B. Marques Angew. Chem. 2006, 118, 356-360;
52. Angew. Chem. Int. Ed. 2006, 45, 348-352;
53. Angew. Chem. Int. Ed. 2006, 45, 348-352;
54. c) J. A. Ma, Angew. Chem. 2003, 115, 4426-4435;
55. Angew. Chem. Int. Ed. 2003, 42, 4290-4299;
56. d) A. Córdova, Acc. Chem. Res. 2004, 37, 102-112.
57. For some anti-Mannich reactions based on metal catalysis, see: a) S. Kobayashi, H. Ishitani, M. Ueno, J. Am. Chem. Soc. 1998, 120, 431-432;
58. b) S. Harada, S. Handa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2005, 117, 4439-4442;
59. Angew. Chem. Int. Ed. 2005, 44, 4365-4368;
60. c) B. M. Trost, J. Jaratjaroonphong, V. Reutrakul, J. Am. Chem. Soc. 2006, 128, 2778-2779.
61. I. Ibrahem, A. Córdova, Chem. Commun. 2006, 1760-1762.
62. H. Zhang, S. Mitsumori, N. Utsumi, M. Imai, N. García-Delgado, M. Midsuf, K. Albertshofer, P. H.-Y. Cheong, K. N. Houk, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2008, 130, 875-886.
63. a) T. Kano, Y. Yamaguchi, O. Tozuda, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 16408-16409;
64. b) T. Kano, Y. Hato, K. Maruoka, Tetrahedron Lett. 2006, 47, 8467-8469.
65. a) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337;
66. b) A. Córdova, S.-I. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867;
67. c) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833. See also reference 12.
68. a) Y. Chi, S. H. Gellman, J. Am. Chem. Soc. 2006, 128, 6804-6805.
69. Recently the same authors reported a diastereoselective version of this reaction in the presence of L-proline as the catalyst and using a chiral N,O-acetal as the iminium precursor: b) Y. Chi, E. P. English, W. C. Pomerantz, W. S. Horne, L. A. Joyce, L. R. Alexander, W. S. Fleming, E. A. Hopkins, S. H. Gellman, J. Am. Chem. Soc. 2007, 129, 6050-6055.
70. I. Ibrahem, G.-L. Zhao, A. Córdova, Chem. Eur. J. 2007, 13, 683-688.
71. J. Alemán, S. Cabrera, E. Maerten, J. Overgaard, K. A. Jørgensen Angew. Chem. 2007, 119, 5616-5619;
72. Angew. Chem. Int. Ed. 2007, 46, 5520-5523.
73. For a case where intramolecular alkylation occurs, see: N. Vignola, B. List, J. Am. Chem. Soc. 2004, 126, 450-451.
74. I. Ibrahem, A. Córdova, Angew. Chem. 2006, 118, 1986-1990;
75. Angew. Chem. Int. Ed. 2006, 45, 1952-1956.
76. For general reviews on organocatalytic conjugate additions, see: a) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716;
77. b) D. Almasi, D. A. Alonso, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 299-365;
78. c) J. L. Vicario, D. Badía, L. Carrillo, Synthesis 2007, 14, 2065-2092.
79. For a review on organocatalytic conjugate additions to nitroalkenes, see: a) S. Sulzer, A. Alexakis, Chem. Commun. 2007, 3123-3135;
80. b) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877-1894.
81. For an application of a recyclable fluorous diphenyl prolinol silyl ether in the same reaction, see: L. Zu, H. Li, J. Wang, X. Yu, W. Wang, Tetrahedron Lett. 2006, 47, 5131-5134.
82. P. Melchiorre, K. A. Jørgensen, J. Org. Chem. 2003, 68, 4151-4157.
83. Y. Chi, S. H. Gellmann, Org. Lett. 2005, 7, 4253-4256.
84. K. Albertshofer, R. Thayumanavan, N. Utsumi, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2007, 48, 693-696.
85. G.-L. Zhao, Y. Xu, H. Sundén, L. Eriksson, M. Sayah, A. Córdova, Chem. Commun. 2007, 734-735.
86. a) S. Mossé, A. Alexakis, Org. Lett. 2005, 7, 4361-4364;
87. b) S. Sulzer-Mossé, M. Tissot, A. Alexakis, Org. Lett. 2007, 9, 3749-3752.
88. C.-L. Cao, X.-L. Sun, J.-L. Zhou, Y. Tang, J. Org. Chem. 2007, 72, 4073-4076.
89. For reviews on organocatalytic enantioselective α- heterofunctionalization of carbonyl compounds, see: a) G. Guillena, D. J. Ramón, Tetrahedron: Asymmetry 2006, 17, 1465-1492;
90. b) M. Marigo, K. A. Jørgensen, Chem. Commun. 2006, 2001-2011.
91. For reviews on α-aminations of carbonyl compounds, see: a) Modern Amination Methods (Ed.: A. Ricci), Wiley-VCH, Weinheim, 2000;
92. b) C. Greck, B. Drouillat, C. Thomassingy, Eur. J. Org. Chem. 2004, 1377-1385.
93. For recent advances in catalytic α-aminations and α-oxygenations of carbonyl compounds, see: J. M. Janey, Angew. Chem. 2005, 117, 4364-4372;
94. Angew. Chem. Int. Ed. 2005, 44, 4292-4300.
95. B. List, J. Am. Chem. Soc. 2002, 124, 5656-5657.
96. A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868-1871;
97. Angew. Chem. Int. Ed. 2002, 41, 1790-1793.
98. For a review on proline-catalyzed α-aminations, see: R. O. Duthaler, Angew. Chem. 2003, 115, 1005-1008;
99. Angew. Chem. Int. Ed. 2003, 42, 975-978.
100. For reviews on nitroso compounds, see: a) P. Zuman, P. Shah, Chem. Rev. 1994, 94, 1621-1641;
101. b) L. Joghyuk, L. Chen, A. H. West, G. B. Richter-Addo, Chem. Rev. 2002, 102, 1019-1065;
102. c) H. Yamamoto, M. Kawasaki, Bull. Chem. Soc. Jpn. 2007, 80, 595-607. Also see Ref. [34].
103. For reviews, see: a) P. Merino, T. Tejero, Angew. Chem. 2004, 116, 3055-3058;
104. Angew. Chem. Int. Ed. 2004, 43, 2995-2997;
105. b) B. Plietker, Tetrahedron: Asymmetry 2005, 16, 3453-3459;
106. c) H. Yamamoto, N. Momiyama, Chem. Commun. 2005, 3514-3525.
107. a) H.-M. Guo, L. Cheng, L.-F. Cun, L.-Z. Ghong, A.-Q. Mi, Y.-Z. Jiang, Chem. Commun. 2006, 429-431;
108. b) T. Kano, M. Ueda, J. Takai, K. Maruoka, J. Am. Chem. Soc. 2006, 128, 6046-6047.
109. C. Palomo, S. Vera, I. Velilla, A. Mielgo, E. Gómez-Bengoa, Angew. Chem. 2007, 119, 8200-8202;
110. Angew. Chem. Int. Ed. 2007, 4636, 8054-8056.
111. I. Ibrahem, G.-L. Zhao, H. Sundén, A. Córdova, Tetrahedron Lett. 2006, 47, 4659-4663.
112. For reviews on asymmetric α-fluorination, see: a) H. Ibrahem, A. Togni, Chem. Commun. 2004, 1147-1155;
113. b) G. K. S. Prakash, P. Beier, Angew. Chem. 2006, 118, 2228-2230;
114. Angew. Chem. Int. Ed. 2006, 45, 2172-2174;
115. c) P. M. Pihko, Angew. Chem. 2006, 118, 558-561;
116. Angew. Chem. Int. Ed. 2006, 45, 544-547.
117. M. Marigo, D. Fielenbach, A. Braunton, A. Kjæsgaard, K. A. Jørgensen, Angew. Chem. 2005, 117, 3769-3772;
118. Angew. Chem. Int. Ed. 2005, 44, 3703-3706.
119. D. D. Steiner, N. Mase, C. F. Barbas III, Angew. Chem. 2005, 117, 3772-3776;
120. Angew. Chem. Int. Ed. 2005, 44, 3706-3710.
121. T. D. Beeson, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 8826-8828.
122. D. Enders, M. R. M. Hüttl, Synlett 2005, 991-993.
123. S. Bertelsen, N. Halland, S. Bachmann, M. Marigo, A. Braunton, K. A. Jørgensen, Chem. Commun. 2005, 4821-4823.
124. W. Wang, H. Li, J. Wang, L. Liao, Tetrahedron Lett. 2004, 45, 8229-8231.
125. A. Armstrong, L. Challinor, J. H. Moir, Angew. Chem. 2007, 119, 5465-5468;
126. Angew. Chem. Int. Ed. 2007, 46, 5369-5372.
127. a) J. N. Fitzner, R. G. Shea, J. E. Fankhauser, P. B. Hopkins, J. Org. Chem. 1985, 50, 417-419;
128. b) R. G. Shea, J. N. Fitzner, J. E. Fankhauser, A. Spaltenstein, P. A. Carpino, R. M. Peevey, D. V. Pratt, B. J. Tenge, P. B. Hopkins, J. Org. Chem. 1986, 51, 5243-5252.
129. a) M. Tiecco, A. Carlone, S. Sternativo, F. Marini, G. Bartoli, P. Melchiorre, Angew. Chem. 2007, 119, 7006-7009;
130. Angew. Chem. Int. Ed. 2007, 46, 6882-6885.
131. For an independent report for the same type of reaction, see: b) H. Sundén, R. Rios, A. Córdova, Tetrahedron Lett. 2007, 48, 7865-7869.
132. For a preliminary work on this reaction with other pyrrolidine derivatives leading to almost racemic products, see: c) W. Wang, J. Wang, H. Li, Org. Lett. 2004, 6, 2817-2820.
133. S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411-4415;
134. Angew. Chem. Int. Ed. 2006, 45, 4305-4309.
135. D. Enders, M. H. Bonten, G. Raabe, Synlett 2007, 885-888.
136. a) S. Karlsson, H.-E. Högberg, Tetrahedron: Asymmetry 2002, 13, 923-926;
137. b) S. Karlsson, H.-E. Högberg, Eur. J. Org. Chem. 2003, 2782-2791.
138. J.-W. Xie, L. Yue, D. Xue, X.-L. Ma, Y.-Ch. Chen, Y. Wu, J. Zhu, J.-G. Deng, Chem. Commun. 2006, 1563-1565.
139. a) K. Mikami, K. Terada in Comprehensive Asymmetric Catalysis, Vol. III (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yammamoto), Springer, Berlin, 1999, pp. 1143-1174;
140. b) K. Mikami, M. Shimizu, Chem. Rev. 1992, 92, 1021;
141. c) D. J. Berrisford, C. Bolm, Angew. Chem. 1995, 107, 1862-1864;
142. Angew. Chem. Int. Ed. Engl. 1995, 34, 1717-1719;
143. d) L. C. Dias, Curr. Org. Chem. 2000, 4, 305-342.
144. H. Gotoh, R. Masui, H. Ogino, M. Shoji, Y. Hayashi, Angew. Chem. 2006, 118, 7007-7010;
145. Angew. Chem. Int. Ed. 2006, 45, 6853-6856.
146. K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244.
147. For recent reviews on enatioselective Diels-Alder reactions, see: a) D. A. Evans, J. S. Johnson in Comprehensive Asymmetric Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999; Vol. III, pp. 1177;
148. b) J. E. Corey, Angew. Chem. 2002, 114, 1724-1741;
149. Angew. Chem. Int. Ed. 2002, 41, 1650-1667;
150. c) Y. Hayashi, Catalytic Asymmetric Diels-Alder Reactions in Cycloaddition Reactions in Organic Synthesis (Eds.: S. Kobayashi, K. A. Jørgensen), Wiley-VCH, Weinheim, Germany, 2002, pp. 5-55.
151. H. Gotoh, Y. Hayashi, Org. Lett. 2007, 9, 2859-2862.
152. B.-C. Hong, M.-F. Wu, H.-C. Tseng, G.-F. Huang, C.-F. Su, J.-H. Liao, J. Org. Chem. 2007, 72, 8459-8471.
153. For reviews, see: a) H. Pellisier, Tetrahedron 2007, 63, 3235-3285;
154. b) I. Coldham, R. Hufton, Chem. Rev. 2005, 105, 2765-2810;
155. c) K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863-910.
156. W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874-9875.
157. S. S. Chow, M. Nevaleinen, C. A. Evans, C. W. Johannes, Tetrahedron Lett. 2007, 48, 277-280.
158. R. Rios, I. Ibrahem, J. Vesely, G.-L. Zhao, A. Córdova, Tetrahedron Lett. 2007, 48, 5701-5705.
159. a) J. L. Vicario, S. Reboredo, D. Badía, L. Carrillo, Angew. Chem. 2007, 119, 5260-5262;
160. Angew. Chem. Int. Ed. 2007, 46, 5168-5170.
161. For [3+2] cycloadditions of azomethine imines, see: b) W. Chen, X.-H. Yuan, R. Li, W. Du, Y. Wu, L.-S. Ding, Y.-C. Chen, Adv. Synth. Catal. 2006, 348, 1818-1822.
162. For reviews on cycloadditions with azomethine ylides, see: a) G. Pandey, P. Banarjee, S. R. Gadre, Chem. Rev. 2006, 106, 4484-4517;
163. b) S. Husinec, V. Savic, Tetrahedron: Asymmetry 2005, 16, 2047-2061;
164. c) C. Nájera, J. M. Sansano, Angew. Chem. 2005, 117, 6428-6432;
165. Angew. Chem. Int. Ed. 2005, 44, 6272-6276.
166. I. Ibrahem, R. Rios, J. Vesely, A. Córdova, Tetrahedron Lett. 2007, 48, 6252-6257.
167. For general information, see: a) P. Pelmuter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
168. For reviews, see: b) M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035;
169. c) J. L. Vicario, L. Badía, L. Carrillo, J. Etxebarria, E. Reyes, N. Ruiz, Org. Prep. Proced. Int. 2005, 37, 513-538;
170. d) L.-W. Xu, C.-G. Xia Eur. J. Org. Chem. 2005, 633-639.
171. I. Ibrahem, R. Rios, J. Vesely, G.-L. Zhao, A. Córdova, Chem. Commun. 2007, 849-851.
172. C. Palomo, M. Oiarbide, R. Halder, M. Kelso, E. Gómez-Bengoa, J. M. García, J. Am. Chem. Soc. 2004, 126, 9188-9189.
173. Y. K. Chen, M. Yoshida, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 9328-9329.
174. J. Vesely, I. Ibrahem, R. Rios, G.-L. Zhao, Y. Xu, A. Córdova, Tetrahedron Lett. 2007, 48, 2193-2198.
175. P. Dinér, M. Nielsen, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 2029-2033;
176. Angew. Chem. Int. Ed. 2007, 46, 1983-1987.
177. For more information on this subject, see: a) I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 8696-8697;
178. b) P. B. Kisanga, P. Ilankumaran, B. M. Fetterly, J. G. Verkade, J. Org. Chem. 2002, 67, 3555-3560.
179. For the conjugate addition of (6S)-methyl δ-lactol to alkylidene-, arylidene-, and heteroarylidene-malonate derivatives, see: a) D. J. Buchanan, D. J. Dixon, F. A. Hernandez-Juan, Org. Lett. 2004, 6, 1357-1360.
180. For the conjugate addition of (6S)-methyl δ-lactol to nitroalkenes, see: b) N. J. Adderley, D. J. Buchanan, D. J. Dixon, D. I. Lainé, Angew. Chem. 2003, 115, 4373-4376;
181. Angew. Chem. Int. Ed. 2003, 42, 4241-4244;
182. c) D. J. Buchanan, D. J. Dixon, F. A. Hernandez-Juan, Org. Biomol. Chem. 2004, 2, 2932-2934;
183. d) D. J. Buchanan, D. J. Dixon, M. S. Scott, D. I. Lainé, Tetrahedron: Asymmetry 2004, 15, 195-197.
184. For the oxa-Michael addition of (-)-N-formylnorephedrine to nitroalkenes, see: e) D. Enders, A. Haertwig, G. Raabe, J. Runsink, Angew. Chem. 1996, 108, 2540-2542;
185. Angew. Chem. Int. Ed. Engl. 1996, 35, 2388-2390;
186. f) D. Enders, A. Haertwig, G. Raabe, J. Runsink, Eur. J. Org. Chem. 1998, 1771-1792;
187. g) D. Enders, A. Haertwig, J. Runsink, Eur. J. Org. Chem. 1998, 1793-1802.
188. D. A. Evans, J. A. Gauchet-Prunet, J. Org. Chem. 1993, 58, 2446-2453.
189. Ch. D. Vanderwal, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 14724-14725.
190. S. Bertelsen, P. Dinér, R. Lyng Johansen, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 1536-1537.
191. For a recent review on sulfa-Michael reactions, see: D. Enders, K. Lüttgen, A. A. Narine, Synthesis 2007, 7, 959-980.
192. M. Marigo, T. Schulte, J. Franzén, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 15710-15711.
193. T. Ishino, T. Oriyama, Chem. Lett. 2007, 36, 550-551.
194. For a general review on phospha-Michael reactions, see: D. Enders, A. Saint-Dizier, M.-I. Lannou, A. Lenzen, Eur. J. Org. Chem. 2006, 29-49.
195. For more information on this topic, see: G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, A. Mazzanti, L. Sambri, P. Melchiorre, Chem. Commun. 2007, 722-724.
196. A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Angew. Chem. 2007, 119, 4588-4590;
197. Angew. Chem. Int. Ed. 2007, 46, 4504-4506.
198. I. Ibrahem, R. Rios, J. Vesely, P. Hammar, L. Eriksson, F. Himo, A. Córdova, Angew. Chem. 2007, 119, 4591-4594;
199. Angew. Chem. Int. Ed. 2007, 46, 4507-4510.
200. S. Bertelsen, M. Marigo, S. Brandes, P. Dinér, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 12973-12980.
201. For an example where a dienamine acts as nucleophile forming a C-C bond at the α-position, see: N. Utsumi, H. Zhang, F. Tanaka, C. F. Barbas III, Angew. Chem. 2007, 119, 1910-1912;
202. Angew. Chem. Int. Ed. 2007, 46, 1878-1880.
203. A. Carlone, M. Marigo, C. North, A. Landa, A. Jørgensen, Chem. Commun. 2006, 4928-4930.
204. X. Linghu, J. J. Kennedy-Smith, F. D. Toste, Angew. Chem. 2007, 119, 7815-7817;
205. Angew. Chem. Int. Ed. 2007, 46, 7671-7673.
206. X. Ma, D. R. Gang, Nat. Prod. Rep. 2004, 21, 752-772.
207. M. Marigo, S. Bertelsen, A. Landa, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 5475-5479.
208. Y. Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. 2007, 119, 5010-5013;
209. Angew. Chem. Int. Ed. 2007, 46, 4922-4925.
210. E. Reyes, H. Jiang, A. Milelli, P. Elsner, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 2007, 119, 9362-9365;
211. Angew. Chem. Int. Ed. 2007, 46, 9202-9205.
212. R. Ríos, I. Ibrahem, J. Vesely, H. Sundén, A. Córdova, Tetrahedron Lett. 2007, 48, 8695-8699.
213. S. Cabrera, J. Alemán, P. Bolze, S. Bertelsen, K. A. Jørgensen, Angew. Chem. 2008, 120, 127-131;
214. Angew. Chem. Int. Ed. 2008, 47, 121-125.
215. G.-L. Zhao, A. Córdova, Tetrahedron Lett. 2006, 47, 7417-7421.
216. For reviews on Hantzsch ester, see: a) H. Adolfsson, Angew. Chem. 2005, 117, 3404-3406;
217. Angew. Chem. Int. Ed. 2005, 44, 3340-3342;
218. b) S.-Li You, Chem. Asian J. 2007, 2, 820-827;
219. c) S. J. Connon, Org. Biomol. Chem. 2007, 5, 3407-3417.
220. For selected reviews on the synthesis of cyclopentanes, see: a) M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49-92;
221. b) C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293-1316.
222. L. Zu, H. Li, H. Xie, J. Wang, W. Jiang, Y. Tang, W. Wang, Angew. Chem. 2007, 119, 3806-3808;
223. Angew. Chem. Int. Ed. 2007, 46, 3732-3734.
224. D. Enders, A. A. Narine, T. R. Benninghaus, G. Raabe, Synlett 2007, 1667-1670.
225. J. Wang, H. Li, H. Xie, L. Zu, X. Shen, W. Wang, Angew. Chem. 2007,119, 9208-9211;
226. Angew. Chem. Int. Ed. 2007, 46, 9050-9053.
227. For recent reviews, see: a) W. A. Donaldson, Tetrahedron 2001, 57, 8589-8627;
228. b) H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977-1050;
229. c) J. M. Fox, N. Yang, Curr. Org. Chem. 2005, 9, 719-732;
230. d) A. Reichelt, S. F. Martin, Acc. Chem. Res. 2006, 39, 433-442.
231. a) R. Ríos, H. Sundén, J. Veseley, G.-L. Zhao, P. Dziedzic, A. Córdova, Adv. Synth. Catal. 2007, 349, 1028-1032;
232. b) H. Xie, L. Zu, H. Li, J. Wang, W. Wang, J. Am. Chem. Soc. 2007, 129, 10886-10894.
233. For reviews of carbenes in asymmetric organocatalysis, see: a) D. Enders, T. Balensiefer, Acc. Chem. Res. 2004, 37, 534-541;
234. b) N. Marion, S. Díez-González, S. P. Nolan, Angew. Chem. 2007, 119, 3046-3058;
235. Angew. Chem. Int. Ed. 2007, 46, 2988-3000.
236. G.-L. Zhao, A. Córdova, Tetrahedron Lett. 2007, 48, 5976-5980.
237. For another contribution on organocatalytic aziridination of α,β-unsturated aldehydes promoted by 1, see: J. Vesely, I. Ibrahem, G.-L. Zhao, R. Rios, A. Córdova, Angew. Chem. 2007, 119, 792-795;
238. Angew. Chem. Int. Ed. 2007, 46, 778-781.
239. R. Rios, J. Vesely, H. Sundén, I. Ibrahem, G.-L. Zhao, A. Córdova, Tetrahedron Lett. 2007, 48, 5835-5839.
240. For an overview and examples, see: a) G. Zeni, R. C. Larok, Chem. Rev. 2004, 104, 2285-2310;
241. b) K. C. Nicolaou, J. A. Pfefferkon, A. J. Roecker, G.-Q. Cao, S. Barluenga, H. J. Mitchell, J. Am. Chem. Soc. 2000, 122, 9939-9953;
242. c) K. C. Nicolaou, J. A. Pfefferkon, H. J. Mitchell, A. J. Roecker, S. Barluenga, G.-Q. Cao, R. L. Affleck, J. E. Lillig, J. Am. Chem. Soc. 2000, 122, 9954-9967;
243. d) K. C. Nicolaou, J. A. Pfefferkon, S. Barluenga, H. J. Mitchell, A. J. Roecker, G.-Q. Cao, J. Am. Chem. Soc. 2000, 122, 9968-9976.
244. T. Govender, L. Hojabri, F. M. Moghaddam, P. I. Arvidsson, Tetrahedron: Asymmetry 2006, 17, 1763-1767.
245. a) H. Sundén, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Córdova, Chem. Eur. J. 2007, 13, 574-581.
246. For another contribution with α,β-unsaturated cyclic ketones, see: b) R. Rios, H. Sundén, I. Ibrahem, A. Córdova, Tetrahedron Lett. 2007, 48, 2181-2184.
247. H. Li, J. Wang, T. E-Nunu, L. Zu, W. Jiang, S. Wei, W. Wang, Chem. Commun. 2007, 507-509.
248. H. Sundén, R. Rios, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Córdova, Adv. Synth. Catal. 2007, 349, 827-832.
249. H. Li, J. Wang, H. Xie, L. Zu, W. Jiang, E. N. Duesler, W. Wang, Org. Lett. 2007, 9, 965-968.
250. S. Brandau, E. Maerten, A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 14986-14991.
251. a) W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc. 2006, 128, 10354-10355;
252. b) R. Rios, H. Sundén, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Córdova, Tetrahedron Lett. 2006, 47, 8547-8551.
253. R. Rios, H. Sundén, I. Ibrahem, G.-L. Zhao, A. Córdova, Tetrahedron Lett. 2006, 47, 8679-8682.
254. H. Li, L. Zu, H. Xie, J. Wang, W. Jiang, W. Wang, Org. Lett. 2007, 9, 1833-1835.
255. a) G. J. Smith, Synthesis 1984, 8, 629-656;
256. b) P. Besse, H. Veschambre, Tetrahedron 1994, 50, 8885-8927.
257. a) Aziridines and Epoxides in Organic Synthesis (Ed.: A. K. Yudin), Wiley-VCH, Weinheim, 2006;
258. b) T. Katutsi in Comprehensive Asymmetric Catalysis, Vol. II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 621-693;
259. c) A. Armstrong, Angew. Chem. 2004, 116, 1484-1486;
260. Angew. Chem. Int. Ed. 2004, 43, 1460-1462.
261. a) M. Marigo, J. Franzén, T. B. Poulsen, W. Zhuang, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 6964-6965;
262. b) W. Zhuang, M. Marigo, K. A. Jørgensen, Org. Biomol. Chem. 2005, 3, 3883-3885.
263. a) H. Sundén, I. Ibrahem, A. Córdova, Tetrahedron Lett. 2006, 47, 99-103;
264. b) G.-L. Zhao, I. Ibrahem, H. Sundén, A. Córdova, Adv. Synth. Catal. 2007, 349, 1210-1224.
265. For a non-enamine-based epoxidation of enones promoted by prolinol derivatives, see: c) A. Lattanzi, Org. Lett. 2005, 7, 2579-2582;
266. d) A. Lattanzi, Adv. Synth. Catal. 2006, 348, 339-346;
267. e) A. Lattanzi, A. Russo, Tetrahedron 2006, 62, 12264-12269;
268. f) Y. Li, X. Liu, Y. Yang, G. Zhao, J. Org. Chem. 2007, 72, 288-291.
269. G.-L. Zhao, P. Dziedzic, I. Ibrahem, A. Córdova, Synlett 2006, 3521-3524.
270. For reviews, see: a) E. N. Jacobsen in Comprehensive Asymmetric Catalysis, Vol. II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 607-618;
271. b) J. B. Sweeney, Chem. Soc. Rev. 2002, 31, 247-258;
272. c) M. McCoull, F. A. Davis, Synthesis 2000, 1347-1365. See also Ref. [121a].
273. D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861-863.
274. D. Enders, M. R. M. Hüttl, J. Runsink, G. Raabe, B. Wendt, Angew. Chem. 2007, 119, 471-473;
275. Angew. Chem. Int. Ed. 2007, 46, 467-469.
276. A. Carlone, S. Cabrera, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 1119-1122;
277. Angew. Chem. Int. Ed. 2007, 46, 1101-1104.
278. General reviews: a) Organic Synthesis in Water (Ed.: P. A. Grieco), Blackie Academic & Profesional, London, 1998;
279. b) U. M. Lindström, Chem. Rev. 2002, 102, 2751-2772;
280. c) C.-J. Li, Chem. Rev. 2005, 105, 3095-3165;
281. d) C. J. Li, L. Cheng, Chem. Soc. Rev. 2006, 35, 68-82.
282. For a critical recent essay, see: D. G. Blackmond, A. Armstrong, V. Coombe, A. Wells, Angew. Chem. 2007, 119, 3872-3874;
283. Angew. Chem. Int. Ed. 2007, 46, 3798-3800.
284. For successful metal catalysis in aqueous systems, see: a) Aqueous-Phase Organometallic Catalysis (Eds.: B. Cornils, W. A. Herrman), WILEY-VCH, Weinheim, 1998;
285. b) S. Kobayashi, C. Ogawa, Chem. Eur. J. 2006, 12, 5954-5960;
286. c) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W.- L- Lam, Chem. Rev. 2002, 102, 2227-2302;
287. d) D. Sinou, Adv. Synth. Catal. 2002, 344, 221-237.
288. Aldol reactions: a) T. J. Dickerson, K. D. Janda, J. Am. Chem. Soc. 2002, 124, 3220-3221;
289. b) H. Torii, M. Nakadai, K. Ishihara, S. Saito, H. Yamamoto, Angew. Chem. 2004, 116, 2017-2020;
290. Angew. Chem. Int. Ed. 2004, 43, 1983-1986;
291. c) P. Dziedzic, W. Zou, J. Hafren, A. Cordova, Org. Biomol. Chem. 2006, 4, 38-40;
292. d) P. M. Pihko, K. M. Laurikainen; A. Usano, A. I. Nyberg, J. A. Kaavi, Tetrahedron 2006, 62, 317-328;
293. A. Usano, A. I. Nyberg, J. A. Kaavi, Tetrahedron 2006, 62, 317-328;
294. e) Y. Hayashi, S. Aratake, T. Okano, J. Takahashi, T. Sumiya, M. Shoji, Angew. Chem. 2006, 118, 5653-5655;
295. Angew. Chem. Int. Ed. 2006, 45, 5527-5529;
296. f) D. Font, C. Jimeno, M. A. Pericàs, Org. Lett. 2006, 8, 4653-4655;
297. g) Y. Wu, Y. Zhang, M. Yu, G. Zhao, S. Wang, Org. Lett. 2006, 8, 4417-4420;
298. h) N. Mase, Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas, J. Am. Chem. Soc. 2006, 128, 734-735.
299. Mannich reaction: i) L. Cheng, X. Wu, Y. Lu, Org. Biomol. Chem. 2007, 5, 1018-1020.
300. Michael reactions: j) N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 4966-4967;
301. k) L. Zu, J. Wang, H. Li, W. Wang, Org. Lett. 2006, 8, 3077-3079;
302. l) Z.-Y. Yan, Y.-N. Niu, H.-L. Wei, L.-Y. Wu, Y.-B. Zhao, Y.-M. Liang, Tetrahedron: Asymmetry 2007, 17, 3288-3293;
303. m) S. Luo, X. Mi, S. Liu, H. Xu, J.-P. Cheng, Chem. Commun. 2006, 3687-3689;
304. n) Y.-J. Cao, Y.-Y. Lai, X. Wang, Y.-J. Li, W.-J. Xiao, Tetrahedron Lett. 2007, 48, 21-24;
305. o) V. Singh, V. K. Singh, Org. Lett. 2007, 9, 1117-1119.
306. For a recent exchange discussion on enamine-based organocatalysis carried out in systems containing water, see: a) A. P. Brogan, T. J. Dikerson, K. D. Janda, Angew. Chem. 2006, 118, 8278-8280;
307. Angew. Chem. Int. Ed. 2006, 45, 8100-8102;
308. b) Y. Hayashi, Angew. Chem. 2006, 118, 8281-8282;
309. Angew. Chem. Int. Ed. 2006, 45, 8103-8104; See also Ref. [127].
310. C. Palomo, A. Landa, A. Mielgo, M. Oiarbide, A. Puente, S. Vera, Angew. Chem. 2007, 119, 8583-8587;
311. Angew. Chem. Int. Ed. 2007, 46, 8431-8435.
312. For the favorable role played by hydrophobic alkyl chains in water-compatible enamine-mediated catalysis, see Ref. [132e,h,j].
313. After submission and manuscript revision the following papers appeared. For a review on enamine catalysis: a) A. Erkkilä, I. Majander, P. M. Phiko, Chem. Rev. 2007, 107, 5416-5470.
314. For a review on iminium catalysis: b) S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569.
315. For an intramolecular nitrogen-based conjugate addition: c) S. Fustero, D. Jiménez, J. Moscardó, S-Catalán, C. del Pozo, Org. Lett. 2007, 9, 5283-5286.
316. For β-amination and selective diamination of α,β- unsaturated aldehydes, see: d) H. Jiang, J. B. Nielsen, M. Nielsen, K. A. Jørgensen, Chem. Eur. J. 2007, 13, 9068-9075.
317. For the β-phosphonylation of enals, see: e) E. Maerten, S. Cabrera, A. Kjaesgaard, K. A. Jørgensen, J. Org. Chem. 2007, 72, 8893-8903.
318. For the Michael addition of nitroalkanes to enals, see: f) H. Gotoh, H. Ishikawa, Y. Hayashi, Org. Lett. 2007, 9, 5307-5309;
319. g) L. Zu, H. Xie, H. Li, J. Wang, W. Wang, Adv. Synth. Catal. 2007, 349, 2660-2664;
320. h) Y. Wang, P. Li, X. Liang, T. Y. Zhang, J. Ye, Chem. Commun. 2008, 1232-1234.
321. For the conjugate addition of aldehydes to nitroalkenes in water, see: i) S. Zhu, S. Yu, D. Ma, Angew. Chem. 2008, 120, 555-558;
322. Angew. Chem. Int. Ed. 2008, 47, 545-548.
323. For an oxidative dearylation of p-substituted phenols followed by an intramolecular Michael addition, see: j) N. T. Vo, R. D. M. Pace, F. O'Hara, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 404-405.
324. For domino thia-Michael aldol reactions, see: k) G.-L. Zhao, J. Vesely, R. Rios, I. Ibrahem, H. Sundén, A. Córdova, Adv. Synth. Catal. 2008, 350, 237-242.
325. For a domino Michael/Michael/aldol condensation sequence, see: l) D. Enders, M. R. M. Hüttl, G. Raabe, J. W. Bats, Adv. Synth. Catal. 2008, 350, 267-279.
326. For a direct crossed-aldol reaction of acetaldehyde, see: m) Y. Hayashi, T. Itoh, S. Aratake, H. Ishikawa, Angew. Chem. 2008, 120, 2112-2114;
327. Angew. Chem. Int. Ed. 2008, 47, 2082-2084.
328. For a formal aza-[3+3] cycloaddition reaction, see: n) Y. Hayashi, H. Gotoh, R. Masui, H. Ishikawa, Angew. Chem. 2008, 120, 4076-4079;
329. Angew. Chem. Int. Ed. 2008, 47, 4012-4015.
330. For a cascade sequence initiated by the 1,4-addition of 2-hydroxy-1,4-napthtoquinones to enals to afford pyranonaphtoquinones and β-lapachones, see: o) M. Rueping, E. Sugiono, E. Merino, Angew. Chem. 2008, 120, 3089-3092;
331. Angew. Chem. Int. Ed. 2008, 47, 3046-3049.
332. For a formal aza [3+3] cycloaddition reaction for the enantioselective formation of enantioenriched piperidines: p) Y. Hayashi, H. Gotoh, R. Masui, H. Ishikawa, Angew. Chem. 2008, 120, 4076-4079;
333. Angew. Chem. Int. Ed. 2008, 47, 4012-4015.
334. For an organocatalytic enamine-iminium-enamine sequence involving cyanoacrylates: q) O. Penon, A. Carlone, A. Mazzanti, M. Locatelli, L. Sambri, G. Bartoli, P. Melchiorre, Chem. Eur. J. 2008, DOI: 10.1002/chem.200800440.
335. For one-pot catalytic asymmetric cascade synthesis of cycloheptane derivatives: r) J. Vesely, R. Rios, I. Ibrahem, G.-L. Zhao, L. Erikson, A. Córdova, Chem. Eur. J. 2008, DOI: 10.1002/chem.200701918.
336. For an organocatalytic double Michael reaction of 7-oxohept-2-enoates and nytrostyrene: s) B.-C. Hong, R. Y. Nimje, M.-F. Wu, A. A. Sadani, Eur. J. Org. Chem. 2008, 1449-1457.
337. For conjugate additions of thioesters to enals: t) D. A. Alonso, S. Kitagaki, N. Utsumi, C. F. Barbas III, Angew. Chem. Int. Ed. 2008, DOI: 10.1002/anie.200801088.
338. For asymmetric Michael reaction of acetaldehyde to nitroalkenes: u) P. García-García, A. Ladépêche, R. Halder, B. List, Angew. Chem. Int. Ed. 2008, DOI: 10.1002/anie.200800847.
339. v) Y. Hayashi, T. Itoh, M. Ohkube, H. Ishikawa, Angew. Chem. Int. Ed. 2008, DOI: 10.1002/anie.200801130.
340. For an organocatalytic one-pot synthesis of substituted 1,4-dihydropyridines: w) P. T. Franke, R.-L. Johansen, S. Bertelsen, K. A. Jørgensen, Chem. Asian J. 2008, 3, 216-264.
341. For the Michael addition of aldehydes to nitroethylene: x) Y. Chi, L. Guo, N. A. Kopf, S. H. Gellman, J. Am. Chem. Soc. 2008, 130, 5608-5609.
342. For the Michael addition of malonates to enals in water: y) A. Ma, S. Zhu, D. Ma, Tetrahedron Lett. 2008, 49, 3075-3077.
343. For a general review on organocatalysis: z) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 2-26;