Cinchona-based primary amine catalysis in the asymmetric functionalization of carbonyl compounds

Angewandte Chemie - International Edition

Volumn 51, Issue 39, 2012, Pages 9748-9770

  Melchiorre, Paolo ^a,b  

^a INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

asymmetric catalysis; carbonyl compounds; cinchona alkaloids; organocatalysis; primary amines

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC REACTION; CINCHONA ALKALOID; EFFICIENCY AND RELIABILITY; FUNCTIONALIZATIONS; HIGH ENANTIOSELECTIVITY; ORGANOCATALYSIS; PRIMARY AMINES; PRIMARY AND SECONDARY AMINE; STERICALLY DEMANDING;

AMINES; AMINO ACIDS; CARBONYL COMPOUNDS; CATALYSTS; REACTION KINETICS; STEREOCHEMISTRY;

CATALYSIS;

EID: 84866492507     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201109036     Document Type: Review

References (253)

1. R. E. Ireland, Organic Synthesis, Prentice-Hall, Englewood Cliffs, 1969.
2. S. Bertelsen, K. A. Jørgensen, Chem. Commun. 2009, 2178-2189
3. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232-6265
4. Angew. Chem. Int. Ed. 2008, 47, 6138-6171
5. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569
6. G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79-87. For a discussion on the mechanisms of the α-, β-, and γ- functionalizations of aldehydes and enals by secondary amines, see
7. M. Nielsen, D. Worgull, T. Zweifel, B. Gschwend, S. Bertelsen, K. A. Jørgensen, Chem. Commun. 2011, 47, 632-649.
8. D. Seebach, U. Grošelj, D. M. Badine, W. B. Schweizer, A. K. Beck, Helv. Chim. Acta 2008, 91, 1999-2034
9. D. Seebach, R. Gilmour, U. Grošelj, G. Deniau, C. Sparr, M.-O. Ebert, A. K. Beck, Helv. Chim. Acta 2010, 93, 603-634
10. M. B. Schmid, K. Zeitler, R. M. Gschwind, Angew. Chem. 2010, 122, 5117-5123
11. Angew. Chem. Int. Ed. 2010, 49, 4997-5003
12. M. B. Schmid, K. Zeitler, R. M. Gschwind, Chem. Sci. 2011, 2, 1793-1803.
13. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396
14. B. List, Tetrahedron 2002, 58, 5573-5590
15. M. Movassaghi, E. N. Jacobsen, Science 2002, 298, 1904-1905.
16. M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804-807
17. Angew. Chem. Int. Ed. 2005, 44, 794-797
18. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284-4287
19. Angew. Chem. Int. Ed. 2005, 44, 4212-4215
20. J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjærsgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 18296-18304; For a Review on the impact diarylprolinol ethers have had in aminocatalysis, see
21. K. L. Jensen, G. Dickmeiss, H. Jiang, Ł. Albrecht, K. A. Jørgensen, Acc. Chem. Res. 2012, 45, 248-264.
22. K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244. See also Ref. [2d].
23. E. N. Jacobsen, D. W. C. MacMillan, Proc. Natl. Acad. Sci. USA 2010, 107, 20618-20619
24. Enantioselective Organocatalysis (Ed.:, P. I. Dalko,), Wiley-VCH, Weinheim, 2007
25. D. W. C. MacMillan, Nature 2008, 455, 304-308.
26. B. List, Angew. Chem. 2010, 122, 1774-1779
27. Angew. Chem. Int. Ed. 2010, 49, 1730-1734
28. C. F. Barbas III, Angew. Chem. 2008, 120, 44-50
29. Angew. Chem. Int. Ed. 2008, 47, 42-47.
30. L.-W. Xu, J. Luo, Y. Lu, Chem. Commun. 2009, 1807-1821. For Reviews focusing on the reasons (and the coincidences) that have brought about the development of cinchona-based primary amines, see
31. L. Jiang, Y.-C. Chen, Catal. Sci. Technol. 2011, 1, 354-365
32. G. Bartoli, P. Melchiorre, Synlett 2008, 1759-1771
33. Y.-C. Chen, Synlett 2008, 1919-1930.
34. The catalysts, in both the pseudo-enantiomeric forms, are easily prepared in a single step by a Mitsunobu reaction of the OH group of readily available natural cinchona alkaloids. For the first synthesis of 9-amino(9-deoxy)-epi- cinchona alkaloids, see:, H. Brunner, J. Bügler, B. Nuber, Tetrahedron: Asymmetry 1995, 6, 1699-1702.
35. Z.-J. Jia, H. Jiang, J.-L. Li, B. Gschwend, Q.-Z. Li, X. Yin, J. Grouleff, Y.-C. Chen, K. A. Jørgensen, J. Am. Chem. Soc. 2011, 133, 5053-5061. For other examples based on trienamine intermediates, see
36. H. Jiang, B. Gschwend, Ł. Albrecht, S. G. Hansen, K. A. Jørgensen, Chem. Eur. J. 2011, 17, 9032-9036
37. Z.-J. Jia, Q. Zhou, Q.-Q. Zhou, P.-Q. Chen, Y.-C. Chen, Angew. Chem. 2011, 123, 8797-8800
38. Angew. Chem. Int. Ed. 2011, 50, 8638-8641
39. Y. Liu, M. Nappi, E. Arceo, S. Vera, P. Melchiorre, J. Am. Chem. Soc. 2011, 133, 15212-15218.
40. G. A. Hamilton, F. H. Westheimer, J. Am. Chem. Soc. 1959, 81, 6332-6333
41. R. A. Laursen, F. H. Westheimer, J. Am. Chem. Soc. 1966, 88, 3426-3430
42. C. Y. Lai, N. Nakai, D. Chang, Science 1974, 183, 1204-1206
43. A. Heine, G. DeSantis, J. G. Luz, M. Mitchell, C.-H. Wong, Science 2001, 294, 369-374, and references therein.
44. K. J. Pedersen, J. Phys. Chem. 1934, 38, 559-571
45. K. J. Pedersen, J. Am. Chem. Soc. 1938, 60, 595-571.
46. F. H. Westheimer, H. Cohen, J. Am. Chem. Soc. 1938, 60, 90-94
47. F. H. Westheimer, W. A. Jones, J. Am. Chem. Soc. 1941, 63, 3283-3286.
48. U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492-493
49. Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497
50. Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621
51. N. Cohen, Acc. Chem. Res. 1976, 9, 412-417, and references therein
52. S. Danishefsky, P. Cain, J. Am. Chem. Soc. 1975, 97, 5282-5283.
53. G. Stork, A. Brizzolara, H. Landesman, J. Szmuszkovicz, R. Terrell, J. Am. Chem. Soc. 1963, 85, 207-222.
54. P. W. Hickmott, Tetrahedron 1982, 38, 1920-2050
55. Chemistry of Enamines (Ed.:, Z. Rappaport,), Wiley, Chichester, 1994.
56. J. Hine, R. A. Evangelista, J. Am. Chem. Soc. 1980, 102, 1649-1655. Enamines are normally stable only when the nitrogen atom does not bear a hydrogen; otherwise, the imine form predominates, see
57. B. Witkop, J. Am. Chem. Soc. 1956, 78, 2873-2882
58. R. A. Clark, D. C. Parker, J. Am. Chem. Soc. 1971, 93, 7257-7261
59. D. R. Boyd, W. B. Jennings, L. C. Waring, J. Org. Chem. 1986, 51, 992-995.
60. J. Hine, Acc. Chem. Res. 1978, 11, 1-7, and references therein.
61. J. Hine, B. C. Menon, J. H. Jensen, J. Mulders, J. Am. Chem. Soc. 1966, 88, 3367-3373
62. J. Hine, F. A. Via, J. Am. Chem. Soc. 1972, 94, 190-194; see also
63. F. Tanaka, R. Thayumanavan, N. Mase, C. F. Barbas III, Tetrahedron Lett. 2004, 45, 325-328. Studies on the iminium ion formation from secondary amines
64. J. Hine, J. Mulders, J. Org. Chem. 1967, 32, 2200-2205
65. J. Hine, R. C. Dempsey, R. A. Evangelista, E. T. Jarvi, J. M. Wilson, J. Org. Chem. 1977, 42, 1593-1599. For the conformational isomerization of imines derived from isobutyraldehyde and primary amines
66. J. Hine, C. H. Yeh, J. Am. Chem. Soc. 1967, 89, 2669-2676.
67. B. Capon, Z.-P. Wu, J. Org. Chem. 1990, 55, 2317-2324, and references therein
68. F. Johnson, Chem. Rev. 1968, 68, 375-413, p. 392 therein
69. J. E. Anderson, D. Casarini, L. Lunazzi, Tetrahedron Lett. 1988, 29, 3141-3144.
70. C. E. Song, Cinchona Alkaloids in Synthesis and Catalysis, Wiley-VCH, Weinheim, 2009
71. T. Marcelli, H. Hiemstra, Synthesis 2010, 1229-1279
72. T. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691-1693.
73. G. Bredig, P. S. Fiske, Biochem. Z. 1912, 46, 7-23.
74. H. Pracejus, Justus Liebigs Ann. Chem. 1960, 634, 9-22.
75. H. Hiemstra, H. Wynberg, J. Am. Chem. Soc. 1981, 103, 417-430
76. H. Wynberg, Top. Stereochem. 1986, 16, 87-129.
77. T. Bürgi, A. Baiker, J. Am. Chem. Soc. 1998, 120, 12920-12926
78. G. D. H. Dijkstra, R. M. Kellogg, H. Wynberg, J. S. Svendsen, I. Marko, K. B. Sharpless, J. Am. Chem. Soc. 1989, 111, 8069-8076
79. A. Urakawa, D. M. Meier, H. Rüegger, A. Baiker, J. Phys. Chem. A 2008, 112, 7250-7255.
80. R. A. Olsen, D. Borchardt, L. Mink, A. Agarwal, L. J. Mueller, F. Zaera, J. Am. Chem. Soc. 2006, 128, 15594-15595.
81. It has already been shown how modulation of the solvent polarity directly reflects on the ability of a cinchona catalyst to induce a preferred handedness in the product formed during an asymmetric transformation, see:, M. Aune, A. Gogoll, O. Matsson, J. Org. Chem. 1995, 60, 1356-1364.
82. X. Tian, C. Cassani, Y. Liu, A. Moran, A. Urakawa, P. Galzerano, E. Arceo, P. Melchiorre, J. Am. Chem. Soc. 2011, 133, 17934-17941. See also
83. H. Brunner, P. Schmidt, M. Prommesberger, Tetrahedron: Asymmetry 2000, 11, 1501-1512.
84. B. Tan, P. J. Chua, Y. Li, G. Zhong, Org. Lett. 2008, 10, 2437-2440
85. B. Tan, X. Zhang, P. J. Chua, G. Zhong, Chem. Commun. 2009, 779-781. Thus, catalysts I-VI are characterized by a dichotomous catalytic behavior. This is because they can execute their catalytic functions using both covalent and noncovalent-based organocatalysis.
86. G. J. S. Evans, K. White, J. A. Platts, N. C. O. Tomkinson, Org. Biomol. Chem. 2006, 4, 2616-2627
87. W. P. Jenks, Catalysis in Chemistry and Enzymology, Section B, Part 1, McGraw-Hill, New York, Chap. 10, 1969.
88. J. Hine, M. S. Cholod, W. K. Chess, Jr., J. Am. Chem. Soc. 1973, 95, 4270-4276
89. J. Hine, F. A. Via, J. Org. Chem. 1977, 42, 1972-1978
90. J. M. Sayer, B. Pinsky, A. Schonbrunn, W. Washtien, J. Am. Chem. Soc. 1974, 96, 7998-8009. See also Ref. [21].
91. S. Warren, B. Zerner, F. H. Westheimer, Biochemistry 1966, 5, 817-823
92. F. C. Kokesh, F. H. Westheimer, J. Am. Chem. Soc. 1971, 93, 7270-7274
93. F. H. Westheimer, Tetrahedron 1995, 51, 3-20
94. M.-H. Ho, J.-F. Ménétret, H. Tsuruta, K. N. Allen, Science 2009, 459, 393-397.
95. S. Mayer, B. List, Angew. Chem. 2006, 118, 4299-4301
96. Angew. Chem. Int. Ed. 2006, 45, 4193-4195
97. N. J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13368-13369.
98. J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. 2007, 119, 393-396
99. Angew. Chem. Int. Ed. 2007, 46, 389-392
100. W. Chen, W. Du, L. Yue, R. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Org. Biomol. Chem. 2007, 5, 816-821.
101. G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403-1405.
102. S. H. McCooey, S. J. Connon, Org. Lett. 2007, 9, 599-602.
103. P. Kwiatkowski, K. DudziÅski, D. ŁyÅwa, Org. Lett. 2011, 13, 3624-3627
104. S. Fustero, C. del Pozo, C. Mulet, R. Lazaro, M. Sánchez- Rosellõ, Chem. Eur. J. 2011, 17, 14267-14272.
105. D.-P. Li, Y.-C. Guo, Y. Ding, W.-J. Xiao, Chem. Commun. 2006, 799-801. For an overview of the catalytic asymmetric Friedel-Crafts alkylations, see
106. Catalytic Asymmetric Friedel-Crafts Alkylations (Eds.:, M. Bandini, A. Umani-Ronchi,), Wiley-VCH, Weinheim, 2009.
107. K. Ishihara, K. Nakano, J. Am. Chem. Soc. 2005, 127, 10504-10505. For the activation of α,β-unsaturated eketones, see
108. H. Kim, C. Yen, P. Preston, J. Chin, Org. Lett. 2006, 8, 5239-5242
109. S. B. Tsogoeva, S. B. Jagtap, Synlett 2004, 2624-2626. See also Ref. [38b].
110. B. List, P. Pojarliev, J. Martin, Org. Lett. 2001, 3, 2423-2425
111. J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740
112. O. Andrey, A. Alexakis, A. Tomassini, G. Bernardinelli, Adv. Synth. Catal. 2004, 346, 1147-1168; see also Ref. [5b].
113. S. B. Tsogoeva, S. Wei, Chem. Commun. 2006, 1451-1453
114. H. Huang, E. N. Jacobsen, J. Am. Chem. Soc. 2006, 128, 7170-7171
115. M. P. Lalonde, Y. Chen, E. N. Jacobsen, Angew. Chem. 2006, 118, 6514-6518
116. Angew. Chem. Int. Ed. 2006, 45, 6366-6370.
117. For cinchona-based primary amines as well as for another general and effective catalyst, namely the cinchona epi-C9-(thio)urea catalyst, the natural stereochemistry at the C9 always provided poor results with respect to the 9-epimer analogues. For an overview of the applications of cinchona thiourea catalyst, see:, S. J. Connon, Chem. Commun. 2008, 2499-2510.
118. D. Seebach, J. GoliÅski, Helv. Chim. Acta 1981, 64, 1413-1423
119. D. Seebach, A. K. Beck, J. Golinski, J. N. Hay, T. Laube, Helv. Chim. Acta 1985, 68, 162-172.
120. A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458-2460; for other applications of chiral secondary amines, see
121. J. B. Tuttle, S. G. Ouellet, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 12662-12663
122. N. Halland, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2002, 67, 8331-8338
123. N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2004, 116, 1292-1297
124. Angew. Chem. Int. Ed. 2004, 43, 1272-1277.
125. J.-W. Xie, L. Yue, W. Chen, W. Du, J. Zhu, J.-G. Deng, Y.-C. Chen, Org. Lett. 2007, 9, 413-415
126. M. W. Paixo, N. Holub, C. Vila, M. Nielsen, K. A. Jørgensen, Angew. Chem. 2009, 121, 7474-7478
127. Angew. Chem. Int. Ed. 2009, 48, 7338-7342
128. C. Liu, Y. Lu, Org. Lett. 2010, 12, 2278-2281.
129. X. Lu, L. Deng, Angew. Chem. 2008, 120, 7824-7827
130. Angew. Chem. Int. Ed. 2008, 47, 7710-7713. See also Ref. [73a].
131. X. Lu, Y. Liu, B. Sun, B. Cindric, L. Deng, J. Am. Chem. Soc. 2008, 130, 8134-8135
132. C. M. Reisinger, X. Wang, B. List, Angew. Chem. 2008, 120, 8232-8235
133. Angew. Chem. Int. Ed. 2008, 47, 8112-8115
134. A. Carlone, G. Bartoli, M. Bosco, F. Pesciaioli, P. Ricci, L. Sambri, P. Melchiorre, Eur. J. Org. Chem. 2007, 5492-5495.
135. P. Ricci, A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Adv. Synth. Catal. 2008, 350, 49-53.
136. Z. Qiao, Z. Shafiq, L. Liu, Z.-B. Yu, Q.-Y. Zheng, D. Wang, Y.-J. Chen, Angew. Chem. 2010, 122, 7452-7456
137. Angew. Chem. Int. Ed. 2010, 49, 7294-7298.
138. Y. K. Chen, M. Yoshida, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 9328-9329. For a metal-based approach with enones, see
139. M. S. Taylor, D. N. Zalatan, A. M. Lerchner, E. N. Jacobsen, J. Am. Chem. Soc. 2005, 127, 1313-1317.
140. The epoxidation of enals driven by iminium/enamine tandem sequence and using a chiral secondary amine is a well-established, enantioselective method:, M. Marigo, J. Franzen, T. B. Poulsen, W. Zhuang, K. A. Jorgensen, J. Am. Chem. Soc. 2005, 127, 6964-6965.
141. E. J. Corey, Angew. Chem. 2002, 114, 1724-1741
142. Angew. Chem. Int. Ed. 2002, 41, 1650-1667
143. Y. Hayashi, Catalytic asymmetric Diels-Alder reactions in Cycloaddition Reactions in Organic Synthesis (Eds.:, S. Kobayashi, K. A. Jørgensen,), Wiley-VCH, Weinheim, 2001.
144. R. P. Singh, K. Bartelson, Y. Wang, H. Su, X. Lu, L. Deng, J. Am. Chem. Soc. 2008, 130, 2422-2423.
145. W. Chen, W. Du, Y. Duan, Y. Wu, S.-Y. Yang, Y.-C. Chen, Angew. Chem. 2007, 119, 7811-7814
146. Angew. Chem. Int. Ed. 2007, 46, 7667-7670.
147. E. Zhang, C.-A. Fan, Y.-Q. Tu, F.-M. Zhang, Y.-L. Son, J. Am. Chem. Soc. 2009, 131, 14626-14627; for a Review on semipinacol rearrangement strategy, see
148. B. Wang, Y.-Q. Tu, Acc. Chem. Res. 2011, 44, 1207-1222.
149. The principle of vinylogy was formulated by Fuson in 1935 as the transmission of electronic effects through a conjugated π-system:, R. C. Fuson, Chem. Rev. 1935, 16, 1-27. In the context of aminocatalysis, this principle accounts for the use of γ-enolisable α,β-unsaturated carbonyl compounds as precursors of nucleophilic dienolate equivalents, formally inverting the usual reactivity of this compound class (vinylogous nucleophilicity).
150. J. Zhou, V. Wakchaure, P. Kraft, B. List, Angew. Chem. 2008, 120, 7768-7771
151. Angew. Chem. Int. Ed. 2008, 47, 7656-7658. For intermolecular aldol reactions promoted by cinchona primary amines, see
152. B.-L. Zheng, Q.-Z. Liu, C.-S. Guo, X.-L. Wang, L. He, Org. Biomol. Chem. 2007, 5, 2913-2915
153. P. Li, J. Zhao, F. Li, A. S. C. Chan, F. Y. Kwong, Org. Lett. 2010, 12, 5616-5619. For aldol reactions under enamine activation by primary amines, see
154. S. Pizzarello, A. L. Weber, Science 2004, 303, 1151
155. S. S. V. Ramasastry, H. Zhang, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2007, 129, 288-289. See also Ref. [16d].
156. C. Agami, H. Sevestre, J. Chem. Soc. Chem. Commun. 1984, 1385-1386
157. C. Agami, N. Platzer, H. Sevestre, Bull. Soc. Chim. Fr. 1987, 2, 358-360
158. B. List, R. A. Lerner, C. F. Barbas III, Org. Lett. 1999, 1, 59-61.
159. T.-Y. Liu, H.-L. Cui, Y. Zhang, K. Jiang, W. Du, Z.-Q. He, Y.-C. Chen, Org. Lett. 2007, 9, 3671-3674; for the pioneering proline-catalyzed α-amination of aldehydes, see
160. A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868-1871
161. Angew. Chem. Int. Ed. 2002, 41, 1790-1793
162. B. List, J. Am. Chem. Soc. 2002, 124, 5656-5657; for proline-catalyzed α-amination of ketones, see
163. N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Bøgevig, K. A. Jørgensen, J. Am. Chem. Soc. 2002, 124, 6254-6255.
164. P. Kwiatkowski, T. D. Beeson, J. C. Conrad, D. W. C. MacMillan, J. Am. Chem. Soc. 2011, 133, 1738-1741.
165. M. Marigo, D. Fielenbach, A. Braunton, A. Kjærsgaard, K. A. Jørgensen, Angew. Chem. 2005, 117, 3769-3772
166. Angew. Chem. Int. Ed. 2005, 44, 3703-3706
167. D. D. Steiner, N. Mase, C. F. Barbas III, Angew. Chem. 2005, 117, 3772-3776
168. Angew. Chem. Int. Ed. 2005, 44, 3706-3710
169. T. D. Beeson, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 8826-8828. The best result in the α-fluorination of cyclohexanone using chiral secondary amines (4-hydroxyproline) led to 56 % yield and 34 % ee, see
170. D. Enders, M. R. M. Hüttl, Synlett 2005, 991-993.
171. A. M. Thayer, Chem. Eng. News 2006, 84, 15-24
172. K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881-1886
173. W. K. Hagmann, J. Med. Chem. 2008, 51, 4359-4369.
174. O. Lifchits, N. Demoulin, B. List, Angew. Chem. 2011, 123, 9854-9857
175. Angew. Chem. Int. Ed. 2011, 50, 9680-9683; for the pioneering contribution on the α-benzoyloxylation of aldehydes under secondary aminocatalysis
176. T. Kano, H. Mii, K. Maruoka, J. Am. Chem. Soc. 2009, 131, 3450-3451. For a recent Review of organocatalyzed asymmetric α-oxygenation of carbonyls, see
177. T. Vilaivan, W. Bhanthumnavin, Molecules 2010, 15, 917-958.
178. L. F. Tietze, G. Brasche, K. M. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006
179. Special Issue on: Rapid Formation of Molecular Complexity in Organic Synthesis:, E. J. Sorensen, H. M. L. Davies, Chem. Soc. Rev. 2009, 38, 2969-3276; Reviews on organocascade reactions
180. C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167-178
181. D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590-1601
182. Angew. Chem. Int. Ed. 2007, 46, 1570-1581
183. A. M. Walji, D. W. C. MacMillan, Synlett 2007, 1477-1489.
184. In addition to creating multiple stereocenters in a one-step process, the combination of multiple asymmetric transformations in a cascade sequence also imparts increased enantiomeric excess to the final product when compared to the corresponding discrete transformations. The Horeau principle provides the mathematical foundation for rationalizing the enantioenrichment observed along successive cascade cycles., J. P. Vigneron, M. Dhaenens, A. Horeau, Tetrahedron 1973, 29, 1055-1059.
185. X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2008, 130, 6070-6071.
186. F. Pesciaioli, F. De Vincentiis, P. Galzerano, G. Bencivenni, G. Bartoli, A. Mazzanti, P. Melchiorre, Angew. Chem. 2008, 120, 8831-8834
187. Angew. Chem. Int. Ed. 2008, 47, 8703-8706
188. F. De Vincentiis, G. Bencivenni, F. Pesciaioli, A. Mazzanti, G. Bartoli, P. Galzerano, P. Melchiorre, Chem. Asian J. 2010, 5, 1652-1656.
189. J. Lv, J. Zhang, Z. Lin, Y. Wang, Chem. Eur. J. 2009, 15, 972-9779.
190. Aziridines and Epoxides in Organic Synthesis (Ed.:, A. Yudin,), Wiley-VCH, New York, 2006. For a synthetically relevant application of cinchona amine-catalyzed epoxidation and aziridination, see
191. H. Jiang, N. Holub, K. A. Jørgensen, Proc. Natl. Acad. Sci. USA 2010, 107, 20630-20635.
192. Q. Cai, C. Zheng, J.-W. Zhang, S.-L. You, Angew. Chem. 2011, 123, 8824-8828
193. Angew. Chem. Int. Ed. 2011, 50, 8665-8669; for a pioneering contribution of organocascade catalysis based on the trapping of the indolinium ion intermediate, see
194. J. F. Austin, S. G. Kim, C. J. Sinz, W. J. Xiao, D. W. C. MacMillan, Proc. Natl. Acad. Sci. USA 2004, 101, 5482-5487.
195. R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820
196. D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Angew. Chem. 2003, 115, 4365-4369
197. Angew. Chem. Int. Ed. 2003, 42, 4233-4237. See also
198. Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5962-5963
199. H. Sundén, R. Rios, Y. Xu, L. Eriksson, A. Cõrdova, Adv. Synth. Catal. 2007, 349, 2549-2555.
200. L.-Y. Wu, G. Bencivenni, M. Mancinelli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7332-7335
201. Angew. Chem. Int. Ed. 2009, 48, 7196-7199.
202. G. Bencivenni, L.-Y. Wu, A. Mazzanti, B. Giannichi, F. Pesciaioli, M.-P. Song, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7336-7339
203. Angew. Chem. Int. Ed. 2009, 48, 7200-7203.
204. S. Kotha, A. C. Deb, K. Lahiri, E. Manivannan, Synthesis 2009, 165-193, and references therein
205. C. V. Galliford, K. A. Scheidt, Angew. Chem. 2007, 119, 8902-8912
206. Angew. Chem. Int. Ed. 2007, 46, 8748-8758.
207. D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861-863. For a different approach to spirooxindoles using cinchona-based amine catalyst, see
208. L.-L. Wang, L. Peng, J.-F. Bai, Q.-C. Huang, X.-Y. Xu, L.-X. Wang, Chem. Commun. 2010, 46, 8064-8066.
209. T. Kano, Y. Tanaka, K. Osawa, T. Yurino, K. Maruoka, Chem. Commun. 2009, 1956-1958. Metal-mediated activation of α-branched unsaturated compounds is generally based on the use of bidentate chelating carbonyl compounds: see for example
210. M. P. Sibi, J. Coulomb, L. M. Stanley, Angew. Chem. 2008, 120, 10061-10063
211. Angew. Chem. Int. Ed. 2008, 47, 9913-9915, and references therein.
212. P. Galzerano, F. Pesciaioli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 8032-8034
213. Angew. Chem. Int. Ed. 2009, 48, 7892-7894.
214. O. Lifchits, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2010, 132, 10227-10229.
215. E. Knoevenagel, Chem. Dtsch. Ber. Ges. 1894, 27, 2345-2346
216. A. Lee, A. Michrowska, S. Sulzer-Mosse, B. List, Angew. Chem. 2011, 123, 1745-1748
217. Angew. Chem. Int. Ed. 2011, 50, 1707-1710.
218. G. Casiraghi, F. Zanardi, G. Appendino, G. Rassu, Chem. Rev. 2000, 100, 1929-1972
219. S. E. Denmark, J. R. Heemstra, Jr., G. L. Beutner, Angew. Chem. 2005, 117, 4760-4777
220. Angew. Chem. Int. Ed. 2005, 44, 4682-4698. For a catalytic asymmetric γ-functionalization of furanones by a direct vinylogous Michael addition
221. B. M. Trost, J. Hitche, J. Am. Chem. Soc. 2009, 131, 4572-4573. For a potentially general method based on nucleophilic phosphine catalysis, see
222. Y. Fujiwara, J. Sun, G. C. Fu, Chem. Sci. 2011, 2, 2196-2198, and references therein.
223. S. Bertelsen, M. Marigo, S. Brandes, P. Dinér, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 12973-12980. For other examples of dienamine catalysis by secondary amines
224. R. M. de Figueiredo, R. Fröhlich, M. Christmann, Angew. Chem. 2008, 120, 1472-1475
225. Angew. Chem. Int. Ed. 2008, 47, 1450-1453
226. K. Liu, A. Chougnet, W.-D. Woggon, Angew. Chem. 2008, 120, 5911-5913
227. Angew. Chem. Int. Ed. 2008, 47, 5827-5829. For a Review
228. D. B. Ramachary, Y. V. Reddy, Eur. J. Org. Chem. 2012, 865-887.
229. N. Utsumi, H. Zhang, F. Tanaka, C. F. Barbas III, Angew. Chem. 2007, 119, 1910-1912
230. Angew. Chem. Int. Ed. 2007, 46, 1878-1880
231. B. Han, Y.-C. Xiao, Z.-Q. He, Y.-C. Chen, Org. Lett. 2009, 11, 4660-4663.
232. G. Bencivenni, P. Galzerano, A. Mazzanti, G. Bartoli, P. Melchiorre, Proc. Natl. Acad. Sci. USA 2010, 107, 20642-20647.
233. The regiocontrolled formation of the extended dienamine t finds support upon related enolization studies demonstrating that, under certain conditions, the selective formation of the thermodynamic exo-cyclic enolate of type t is strongly favored over both the endo-isomer and the kinetic cross-conjugated dienolate. This inherent behavior of β-substituted cyclohexenones has found a wonderful application in the direct, vinylogous aldol reaction, see:, S. Saito, M. Shiozawa, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 813-814. In analogy with the report by Yamamoto and co-workers, the complete γ-site selectivity induced by the amine V may arise from catalyst steric effects, which inhibit base deprotonation at the α' position, while thermodynamic factors account for the formation of the reactive exo-dienamine t.
234. D.-Q. Xu, A.-B. Xia, S.-P. Luo, J. Tang, S. Zhang, J.-R. Jiang, Z.-Y. Xu, Angew. Chem. 2009, 121, 3879-3882
235. Angew. Chem. Int. Ed. 2009, 48, 3821-3824. See also
236. G. N. Stowe, K. D. Janda, Tetrahedron Lett. 2011, 52, 2085-2087.
237. G. Bergonzini, S. Vera, P. Melchiorre, Angew. Chem. 2010, 122, 9879-9882
238. Angew. Chem. Int. Ed. 2010, 49, 9685-9688.
239. P. G. Cozzi, F. Benfatti, L. Zoli, Angew. Chem. 2009, 121, 1339-1342
240. Angew. Chem. Int. Ed. 2009, 48, 1313-1316; for related studies
241. R. R. Shaikh, A. Mazzanti, M. Petrini, G. Bartoli, P. Melchiorre, Angew. Chem. 2008, 120, 8835-8838
242. Angew. Chem. Int. Ed. 2008, 47, 8707-8710
243. A. R. Brown, W.-H. Kuo, E. N. Jacobsen, J. Am. Chem. Soc. 2010, 132, 9286-9288.
244. Chiral secondary amine catalysis has been used in the γ-alkylation of α-unbranched enals, see:, J. Stiller, E. Marqués-Lõpez, R. P. Herrera, R. Fröhlich, C. Strohmann, M. Christmann, Org. Lett. 2011, 13, 70-73.
245. X.-F. Xiong, Q. Zhou, J. Gu, L. Dong, T.-Y. Liu, Y.-C. Chen, Angew. Chem. 2012, 124, 4477-4480
246. Angew. Chem. Int. Ed. 2012, 51, 4401-4404.
247. K. Nishide, M. Ozeki, H. Kunishige, Y. Shigeta, P. K. Patra, Y. Hagimoto, M. Node, Angew. Chem. 2003, 115, 4653-4655
248. Angew. Chem. Int. Ed. 2003, 42, 4515-4517. For a Review on sulfa-Michael reactions, see
249. D. Enders, K. Lüttgen, A. Narine, Synthesis 2007, 959-980.
250. B. Simmons, A. M. Walji, D. W. C. MacMillan, Angew. Chem. 2009, 121, 4413-4417
251. Angew. Chem. Int. Ed. 2009, 48, 4349-4353
252. Y. Chi, S. T. Scroggins, J. M. J. Fréchet, J. Am. Chem. Soc. 2008, 130, 6322-6323.
253. R. R. Knowles, E. N. Jacobsen, Proc. Natl. Acad. Sci. USA 2010, 107, 20678-20685.