Organocatalytic Enantioselective Morita-Baylis-Hillman Reactions

Enantioselective Organocatalysis: Reactions and Experimental Procedures

Volumn , Issue , 2007, Pages 151-187

  Menozzi, Candice ^a   Dalko, Peter I ^b  

^a PSL RESEARCH UNIVERSITY   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Addition of ketones and aldehydes to activated olefins; Asymmetric Aza MBH reactions; Chiral amine catalysts; Diastereoselectivity; Organocatalytic enantioselective Morita Baylis Hillman (MBH) reactions; Reaction mechanism

Indexed keywords

EID: 37649016631     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527610945.ch5     Document Type: Chapter

References (164)

1. For general reviews, see: L.J. Brzezinski, S. Rafel, J.W. Leahy, J. Am. Chem. Soc. 1997, 119, 4317-4318;
2. E. Ciganek. The Catalyzed α-Hydroxylation and α-Aminoalkylation of Activated Olefins (The Morita-Baylis-Hillman Reaction). In: L.A. Paquette (Ed.), Organic Reactions. Wiley, New York, 1997, Vol. 51, p. 201;
3. D. Basavaiah, P.D. Rao, R.S. Hyma, Tetrahedron 1996, 52, 8001-8062;
4. P. Langer, Angew. Chem. Int. Ed. 2000, 39, 3049-3052;
5. A. Gilbert, T.W. Heritage, N.S. Isaacs, Tetrahedron: Asymmetry 1991, 2, 969-972;
6. D. Basavaiah, A.J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811-891;
7. K.Y Lee, S. Gowrisankar, J.N. Kim, Bull. Korean Chem. Soc. 2005, 26, 1481-1490.
8. For related chalchogene-mediated additions, see: A. Kamimura, J. Synth. Org. Chem. Jpn. 2004, 62, 705-715.
9. K. Morita, Z. Suzuki, H. Hirose, Bull. Chem. Soc. Jpn. 1968, 41, 2815-2815;
10. K. Morita, Japan Patent 6803364, 1968; Chem. Abstr. 1968, 69, 58828s.
11. R. Oda, T. Kawabata, S. Tanimoto, Tetrahedron Lett. 1964, 5, 1653-1657.
12. A.B. Baylis, M.E.D. Hillman; German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174q.
13. S.E. Drewes, N.D. Emslie, J. Chem. Soc. Perkins Trans. 1 1982, 2079-2085;
14. H.M.R. Hoffmann, J. Rabe, Angew. Chem. Int. Ed. Engl. 1983, 22, 795-796.
15. G.E. Keck, D.S. Welch, Org. Lett. 2002, 4, 3687-3690.
16. H. Amri, J. Villieras, Tetrahedron Lett. 1986, 27, 4307-4308;
17. D. Basavaiah, T.K. Bharathi, V.V.L. Gowriswari, Synth. Commun. 1987, 17, 1893.
18. D. Basavaiah, V.V.L. Gowriswari, Tetrahedron Lett. 1986, 27, 2031-2032.
19. P. Auvray, P. Knochel, J.F. Normant, Tetrahedron Lett. 1986, 27, 5095-5098.
20. A. Weichert, H.M.R. Hoffmann, J. Org. Chem. 1991, 56, 4098-4112.
21. S.Z. Wang, K. Yamamoto, H. Yamada, T. Takahashi, Tetrahedron 1992, 48, 2333-2348.
22. H. Amri, M.M. El Gaied, J. Villieras, Synth. Commun. 1990, 20, 659.
23. M.K. Kundu, S.B. Mukherjee, N. Balu, R. Padmakumar, S.V. Bhat, Synlett 1994, 444-445;
24. C. Yu, L. Hu, J. Org. Chem. 2002, 67, 219-223;
25. C. Faltin, E.M. Fleming, S.J. Connon, J. Org. Chem. 2004, 69, 6496-6499.
26. J.S. Hill, N.S. Isaacs, Tetrahedron Lett. 1986, 27, 5007-5010;
27. G.M. Strunz, R. Bethell, G. Sampson, P. White, Can. J. Chem. 1995, 73, 1666-1674.
28. S. Tsuboi, S. Takatsuka, M. Utaka, Chem Lett. 1988, 2003;
29. S. Tsuboi, H. Kuroda, S. Takatsuka, T. Fukawa, T. Sakai, M. Utaka, J. Org. Chem. 1993, 58, 5952-5957;
30. G.-L. Zhao, M. Shi, J. Org. Chem. 2005, 70, 9975-9984.
31. Y. Matsuya, K. Hayashi, H. Nemoto, J. Am. Chem. Soc. 2003, 125, 646-647;
32. S. Xue, Q.-F. Zhou, L. Li, Q.-X. Guo, Synlett 2005, 2990-2992.
33. T.G. Back, D.A. Rankic, J.M. Sorbetti, J.E. Wulff, Org. Lett. 2005, 7, 2377-2379.
34. D. Basavaiah, V.V.L. Gowriswari, Synth. Commun. 1989, 19, 2461-2465;
35. C. Grundke, H.M.R. Hoffmann, Chem. Ber. 1987, 120, 1461-1461;
36. M. Shi, W. Zhang, Tetrahedron 2005, 61, 11887-11894.
37. A.S. Golubev, M.V. Galakhov, A.F. Kolomiets, A.V. Fokin, Izv. Akad. Nauk, Ser. Khimi. 1992, 12, 2763-2767.
38. P. Perlmutter, C.C. Teo, Tetrahedron Lett. 1984, 25, 5951-5952;
39. K. Yamamoto, M. Takagi, M. Tsuji, Bull. Chem. Soc. Jpn. 1988, 61, 319;
40. M. Takagi, K. Yamamoto, Tetrahedron 1991, 47, 8869-8882.
41. J.S. Hill, N.S. Isaacs, J. Chem. Res. 1988, 330-330.
42. W.D. Lee, K.S. Yang, K.M. Chen, Chem. Commun. 2001, 1612-1613.
43. S.E. Drewes, G.H.P. Roos, Tetrahedron 1988, 44, 4653-4670.
44. V.K. Aggarwal, I. Emme, S.Y. Fulford, J. Org. Chem. 2003, 68, 692-700.
45. V.K. Aggarwal, A. Mereu, Chem. Commun. 1999, 2311-2312.
46. F. Rezgui, M.M. El Gaied, Tetrahedron Lett. 1998, 39, 5965-5966;
47. R. Octavio, M.A. de Souza, M.L. Vasconcellos, Synth. Commun. 2003, 33, 1383-1389.
48. S. Luo, B. Zhang, J. He, A. Janczuk, P.G. Wang, J. Cheng, Tetrahedron Lett. 2002, 43, 7369-7371;
49. For the use of 1-methylimidazole 3-N-oxide, see: Y.-S. Lin, C.-W. Liu, T.Y.R. Tsai, Tetrahedron Lett. 2005, 46, 1859-1861.
50. N.E. Leadbeater, C. Van der Pol, J. Chem. Soc. Perkin Trans. 1 2001, 2831-2835;
51. R.S. Grainger, N.E. Leadbeater, A.M. Pamies, Catal. Commun. 2002, 3, 449-452.
52. S. Luo, X. Mi, G.W. Peng, J.P. Cheng, Tetrahedron Lett. 2004, 45, 5171-5174.
53. S.-H. Zhao, Z.-B. Chen, Synth. Commun. 2005, 35, 3045-3053.
54. T. Miyakoshi, H. Omichi, S. Saito, Nippon Kagaku Kaishi 1979, 748-753; Chem. Abstr. 1979, 91, 12336Od.
55. S. Rafel, J.W. Leahy, J. Org. Chem. 1997, 62, 1521-1522;
56. M. Shi, Y.-H. Liu, Org. Biomol. Chem. 2006, 4, 1468;
57. Z. He, X. Tang, Y. Chen, Z. He, Adv. Synth. Catal. 2006, 348, 413-417.
58. R.J.W. Schuurman, A.V. den Linden, R.P.F. Grimbergen, R.J.M. Nolte, H.W. Scheeren, Tetrahedron 1996, 52, 8307-8314;
59. N.S. Isaacs, Tetrahedron 1991, 47, 8463-8497;
60. Y. Hayashi, K. Okado, I. Ashimine, M. Shoji, Tetrahedron Lett. 2002, 43, 8683-8686;
61. See also: M. Shi, Y.-H. Liu, Org. Biomol. Chem. 2006, 4, 1468-1470.
62. G.H.P. Roos, P. Rampersadh, Synth. Commun. 1993, 23, 1261-1266;
63. W.P. Almeida, F. Coehlo, Tetrahedron Lett. 1998, 39, 8609-8612;
64. F. Coehlo, W.P. Almeida, D. Veronese, C.R. Mateus, E.C. Silva Lopes, R.C. Rossi, G.P.C. Silveira, C.H. Pavam, Tetrahedron 2002, 58, 7437-7447.
65. V.K. Aggarwal, A. Mereu, G.J. Tarver, J. Org. Chem. 1998, 63, 7183-7189.
66. K.-S. Yang, W.-D. Lee, J.-F. Pan, K.-M. Chen, J. Org. Chem. 2003, 68, 915-919.
67. V.K. Aggarwal, D.K. Dean, A. Mereu, R. Williams, J. Org. Chem. 2002, 67, 510-514.
68. D.J. Maher, S.J. Connon, Tetrahedron Lett. 2004, 45, 1301-1305.
69. H.S. Byurn, K.C. Reddy, R. Bitman, Tetrahedron Lett. 1994, 35, 1371-1374;
70. J. Auge, N. Lubin, A. Lubineau, Tetrahedron Lett. 1994, 35, 7947-7948;
71. J. Cai, Z. Zhou, G. Zhao, C. Tang, Org. Lett. 2002, 4, 4723-4725;
72. D. Basavaiah, M. Krishnamacharyulu, A. Rao, Synth. Commun. 2000, 30, 2061-2069;
73. C.Z. Yu, B. Liu, L.Q. Hu, J. Org. Chem. 2001, 66, 5413-5418.
74. Roos and Rampersadh have observed that "gentle warming" effects a marked rate increase in the reaction with acetaldehyde and a slight increase with other aldehydes, but they also observed polymerization at temperatures above 43 °C. G.H.P. Roos, P. Rampersadh, Synth. Commun. 1993, 23, 1261-1266.
75. P.R. Krishna, A. Manjuvani, V. Kannan, G.V.M. Sharma, Tetrahedron Lett. 2004, 45, 1183-1185.
76. A. Porzelle, C.M. Williams, B.D. Schwartz, I.R. Gentle, Synlett 2005, 2923-2926.
77. X. Mi, S. Luo, J.-P. Cheng, J. Org. Chem. 2005, 70, 2338-2341;
78. J.-C. Hsu, Y.-H. Yen, Y.-H. Chu, Tetrahedron Lett. 2004, 45, 4673-4676;
79. A. Kumar, S.S. Pawar, J. Mol. Catal. A: Chemical 2004, 211, 43-47;
80. E.J. Kim, S.Y. Ko, C.E. Song, Helv. Chim. Acta 2003, 86, 894-899;
81. V.K. Aggarwal, I. Emme, A. Mereu, Chem. Commun. 2002, 1612-1613;
82. J.N. Rosa, C.A. Afonso, A.G. Santos, Tetrahedron, 2001, 57, 4189-4193.
83. J.S. Hill, N.S. Isaacs, J. Phys. Org. Chem. 1990, 3, 285-288; For earlier discussions on the mechanism of the MBH reaction, see Ref. [6b].
84. P.T. Kaye, M.L. Bode, Tetrahedron Lett. 1991, 32, 5611-5614;
85. Y. Fort, M.C. Berthe, P. Caubere, Tetrahedron 1992, 48, 6371-6384.
86. L.S. Santos, C.H. Pavam, W.P. Almeida, F. Coehlo, M.N. Eberlin, Angew. Chem. Int. Ed. 2004, 43, 4330-4333.
87. The term was coined in analogy of pharmaceutical compound classes that are active against a number of different biological targets. See: T.P. Yoon, E.N. Jacobsen, Science 2003, 299, 1691-1693.
88. S.E. Drewes, N.D. Emslie, N. Karodia, A.A. Khan, Chem. Ber. 1990, 123, 1447-2456;
89. P. Perlmutter, E. Puniani, G. Westman, Tetrahedron Lett. 1996, 37, 1715-1718.
90. V.K. Aggarwal, S.Y. Fulford, G.C. Lloyd-Jones, Angew. Chem. Int. Ed. 2005, 44, 1706-1708.
91. Y. Takemoto, Org. Biomol. Chem. 2005, 3, 4299-4306.
92. K.E. Price, S.J. Broadwater, H.M. Jung, D.T. McQuade, Org. Lett. 2005, 7, 147-150;
93. K.E. Price, S.J. Broadwater, B.J. Walker, D.T. McQuade, J. Org. Chem. 2005, 70, 3980-3987.
94. G. Roos, T. Manickum, Synth. Commun. 1991, 21, 2269-2274;
95. S.E. Drewes, A. Khan, K. Rowland, Synth. Commun. 1993, 23, 183.
96. B. Alcaide, P. Almendros, C. Aragoncillo, J. Org. Chem. 2001, 66, 1612-1620;
97. B. Alcaide, P. Almendros, C. Aragoncillo, R. Rodríguez-Acebes, J. Org. Chem. 2004, 69, 826-831.
98. F. Coelho, G. Diaz, C.A.M. Abella, W.P. Almeida, Synlett 2006, 435-439;
99. W.P. Almeida, F. Coelho, Tetrahedron Lett. 2003, 44, 937-937.
100. See for example: M. Shi, J.-K. Jiang, Y.-S. Feng, Org. Lett. 2000, 2, 2397-2400;
101. M. Ono, K. Nishimura, Y. Nagaoka, K. Tomioka, Tetrahedron Lett. 1999, 40, 1509-1512;
102. T. Iwama, S.-I. Tsijiyama, H. Kinoshita, K. Kanamatsu, Y. Tsurukami, T. Iwamura, S.-I. Watanabe, T. Kataoka, Chem. Pharm. Bull. 1999, 47, 956-961;
103. M. Kawamura, S. Kobayashi, Tetrahedron Lett. 1999, 40, 1539-1542;
104. E.P. Kündig, L.H. Xu, P. Romanens, G. Bernardinelli, Tetrahedron Lett. 1993, 34, 7049-7052;
105. L.M. Walsh, C.L. Winn, J.M. Goodman, Tetrahedron Lett. 2002, 43, 8219-8222.
106. T. Oishi, H. Oguri, M. Hirama, Tetrahedron: Asymm. 1995, 6, 1241-1244.
107. A.G.M. Barrett, A.S. Cook, A. Kamimura, Chem. Commun. 1998, 2533-2534.
108. A.G.M. Barrett, P. Dozzo, A.J.P. White, D.J. Williams, Tetrahedron 2002, 58, 7303-7313.
109. H.M.R. Hoffmann, J. Rabe, J. Angew. Chem. Int. Ed. Engl. 1985, 24, 94-109.
110. S.E. Drewes, S.D. Freese, N.D. Emslie, G.H.P. Roos, Synth. Commun. 1988, 18, 1565-1572;
111. M. Bailey, I.E. Marko, W.D. Ollis, P.R. Rassmussen, Tetrahedron Lett. 1990, 31, 4509-4512;
112. The use of AcOH as co-catalyst was described earlier: H.M.R. Hoffmann, J. Org. Chem. 1988, 53, 3701-3710.
113. I.E. Marko, P.R. Giles, N.J. Hindley, Tetrahedron 1997, 53, 1015-1024.
114. P.R. Krishna, V. Kannan, P.V.N. Reddy, Adv. Synth. Catal. 2004, 346, 603-606.
115. Y. Wabuchi, M. Nakatani, S. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219-10220;
116. A. Nakano, S. Kawahara, K. Morokuma, M. Nakatami, Y. Iwabuchi, K. Takahashi, J. Ishihara, S. Hatakeyama, Tetrahedron 2006, 62, 381-389.
117. β-ICD can be synthesized in approx. 60% yield in one step from (+)-quinidine by heating with 10 equiv. of KBr in 85% phosphoric acid at 100 °C for 5 days [64a].
118. F. Ameer, S.E. Drewes, S. Freese, P.T. Kaye, Synth. Commun. 1988, 18, 495-500.
119. Y. Iwabuchi, M. Sugihara, T. Esumi, S. Hatakeyama, Tetrahedron Lett. 2001, 42, 7867-7871.
120. Y. Iwabuchi, M. Furukawa, T. Esumi, S. Hatakeyama, Chem. Commun. 2001, 2030-2031.
121. M. Shi, J.K. Jiang, Tetrahedron: Asymm. 2002, 13, 1941-1947.
122. C.M. Mocquet, S.L. Warriner, Synlett 2004, 356-357.
123. C.E. Aroyan, M.M. Vasbinder, S.J. Miller, Org. Lett. 2005; 7, 3849-3851;
124. J.E. Imbriglio, M.M. Vasbinder, S.J. Miller, Org. Lett. 2003, 5, 3741-3743.
125. For an excellent review, see: S.J. Miller, Acc. Chem. Res. 2004, 37, 601-610.
126. M. Shi, J.-K. Jiang, C.-Q. Li, Tetrahedron Lett. 2002, 43, 127-130.
127. For earlier intramolecular MBH reactions, see: S.E. Drewes, O.L. Njamela, N.D. Emslie, N. Ramesar, J.S. Field, Synth. Commun. 1993, 23, 2807-2815;
128. G.P. Black, F. Dinon, S. Fratucello, P.J. Murphy, M. Nielson, H.L. Williams, N.D.A. Walshe, Tetrahedron Lett. 1997, 38, 8561-8564;
129. F. Dinon, E. Richards, P.J. Murphy, D.E. Hibbs, M.B. Hursthouse, K.M.A. Malik, Tetrahedron Lett. 1999, 40, 3279-3282;
130. E.L. Richards, P.J. Murphy, F. Dinon, S. Fratucello, P.M. Brown, T. Gelbrich, M.B. Hursthouse, Tetrahedron 2001, 57, 7771-7784.
131. S.-H. Chen, B.-C. Hong, C.-F. Su, S. Sarshar, Tetrahedron Lett. 2005, 46, 8899-8903.
132. Y. Takemoto, Org. Biomol. Chem. 2005, 3, 4299-4306.
133. T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673;
134. T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119-125;
135. Y. Hoashi, T. Okino, Y. Takemoto, Angew. Chem. Int. Ed. 2005, 44, 4032-4035.
136. T. Okino, S. Nakamura, T. Furukawa, Y. Takemoto, Org. Lett. 2004, 6, 625-627.
137. J. Wang, H. Li, X. Yu, L. Zu, W. Wang, Org. Lett. 2005, 7, 4293-4296.
138. A.G. Wenzel, M.P. Lalonde, E.N. Jacobsen, Synlett 2003, 1919-1922.
139. Y. Sohtome, A. Tanatani, Y. Hashimoto, K. Nagasawa, Tetrahedron Lett. 2004, 45, 5589-5592.
140. For revews, see: T. Clark, C. Landis, Tetrahedron: Asymm. 2004, 15, 2123-2137;
141. M. Oestreich, Nachr. Chem. 2004, 52, 1257-1260;
142. J.L. Methot, W.R. Roush, Adv. Synth. Catal. 2004, 346, 1035-1050; See also:
143. X. Zhang (ed.), 'Chiral Phosphorus Ligands'; Thematic issue; Tetrahedron: Asymm. 2004, 15, 2099-2311.
144. F. Roth, P. Gygax, G. Frater, Tetrahedron Lett. 1992, 33, 1045-1048.
145. W.-D. Teng, R. Huang, C.K.-W. Kwong, M. Shi, P.H. Toy, J. Org. Chem., 2006, 71, 368-371.
146. T. Hayase, T. Shibata, K. Soai, Y. Wakatsuki, Chem. Commun. 1998, 1271-1272.
147. W. Li, Z. Zhang, D. Xiao, X. Zhang, J. Org. Chem. 2000, 65, 3489-3496.
148. For a recent review on mannitol derivatives in enantiocatalytic reactions, see: S. Castillon, C. Claver, Y. Diaz, Chem. Soc. Rev. 2005, 34, 702-713.
149. Y.M.A. Yamada, S. Ikegami, Tetrahedron Lett. 2000, 41, 2165-2169.
150. N.T. McDougal, S.E. Schaus, J. Am. Chem. Soc. 2003, 125, 12094-12095.
151. N.T. McDougal, W.L. Trevellini, S.A. Rodgen, L.T. Kliman, S.E. Schaus, Adv. Synth. Catal. 2004, 346, 1231-1240.
152. Catalysts can be prepared by hydrogenation of naphthol derivatives over PtO2 in acetic acid.
153. M. Shi, Y.M. Xu, Chem. Commun. 2001, 1876-1877.
154. P. Buskens, J. Klankermayer, W. Leitner, J. Am. Chem. Soc. 2005, 127, 16762-16763.
155. S. Kawahara, A. Nakano, T. Esumi, Y. Iwabuchi, S. Hatakeyama, Org. Lett. 2003, 5, 3103-3105.
156. M. Shi, Y.M. Xu, Angew. Chem. Int. Ed. Engl. 2002, 41, 4507-4510;
157. M. Shi, Y.-M. Xu, Y.-L. Shi, Chem. Eur.J. 2005, 11, 1794-1802.
158. K. Matsui, S. Takizawa, H. Sasai, J. Am. Chem. Soc. 2005, 127, 3680-3681.
159. I.T. Raheem, E.N. Jacobsen, Adv. Synth. Catal. 2005, 347, 1701-1708.
160. For a review, see: M. Shi, L.H. Chen, Pure Appl. Chem. 2005, 77, 2105-2110.
161. M. Shi, L.-H. Chen, Chem. Commun. 2003, 1310-1311;
162. M. Shi, L.-H. Chen, C.-Q. Li, J. Am. Chem. Soc. 2005, 127, 3790-3800.
163. M. Shi, L.H. Chen, W.D. Teng, Adv. Synth. Catal. 2005, 347, 1781-1789.
164. M. Shi, C.Q. Li, Tetrahedron: Asymm. 2005, 16, 1385-1391.