Organocatalytic Sigmatropic reactions

Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications

Volumn 3-3, Issue , 2013, Pages 1191-1224

  Valero, Guillem ^a   Moyano, Albert ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Aza Cope rearrangement; Aza Petasis Ferrier rearrangement; Claisen rearrangement; Pinacol rearrangement; Sigmatropic rearrangements; Steglich rearrangement

Indexed keywords

AZA-COPE REARRANGEMENT; CLAISEN REARRANGEMENT; FERRIER REARRANGEMENT; PINACOL REARRANGEMENTS; SIGMATROPIC REARRANGEMENTS; STEGLICH REARRANGEMENT;

EID: 84948830677     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527658862.ch40     Document Type: Chapter

References (155)

1. Trost, B.M., Fleming, I., and Pattenden, G. (eds) (1991) Comprehensive Organic Synthesis, vol. 3, section 3, and vol. 5, section 7, Pergamon Press, Oxford.
2. Enders, D., Knopp, M., and Schiffers, R. (1996) Tetrahedron: Asymmetry, 7, 1847-1882.
3. Nakai, T. and Tomooka, K. (1997) Pure Appl. Chem., 69, 595-600.
4. Ito, H. and Taguchi, T. (1999) Chem. Soc. Rev., 28, 43-50.
5. Allin, S.M. and Baird, R.D. (2001) Curr. Org. Chem., 5, 395-415 .
6. Nubbemeyer, U. (2003) Synthesis, 961-1008.
7. Castro, A.M.M. (2004) Chem. Rev., 104, 2939-3002.
8. Hajos, Z.G. and Parrish, D.R. (1974) J. Org. Chem., 39, 1615-1621.
9. Eder, U., Sauer, G., and Wiechert, R. (1971) Angew. Chem., Int. Ed. Engl., 10, 496-497 .
10. List, B., Lerner, R.A., and Barbas, C.F. III (2000) J. Am. Chem. Soc., 122, 2395-2396.
11. Córdova, A., Notz, W., and Barbas, C.F. III (2002) J. Org. Chem., 67, 301-303.
12. Northrup, A.B. and MacMillan, D.W.C. (2002) J. Am. Chem. Soc., 124, 6798-6799;
13. For reviews on organocatalytic aldol reactions, see: (f) Guillena, G., Nájera, C., and Ramón, D.J. (2007) Tetrahedron: Asymmetry, 18, 2249-2293.
14. Zlotin, S.G., Kucherenko, A.S., and Beletskaya, I.P. (2009) Russ. Chem. Rev., 78, 737-784.
15. Bhanushali, M. and Zhao, C.-G. (2011) Synthesis, 1815-1830.
16. List, B. (2000) J. Am. Chem. Soc., 122, 9336-9337.
17. Ting, A. and Schaus, S.E. (2007) Eur. J. Org. Chem., 5797-5815.
18. Verkade, J.M.M., Lieke, J.C.V.H., Quadfl ieg, P.J.L.M., and Rutjes, F.P.J.T. (2008) Chem. Soc. Rev., 37, 29-41.
19. Ahrendt, K.A., Borths, C.J., and MacMillan, D.W.C. (2000) J. Am. Chem. Soc., 122, 4243-4244.
20. Northrup, A.B. and MacMillan, D.W.C. (2002) J. Am. Chem. Soc., 124, 2458-2460.
21. Kinsman, A.C. and Kerr, M.A. (2003) J. Am. Chem. Soc., 125, 14120-14125.
22. Ishihara, K. and Nakano, K. (2005) J. Am. Chem. Soc., 127, 10504-10505.
23. Sundén, H., Ibrahem, I., Eriksson, L., and Córdova, A. (2005) Angew. Chem., Int. Ed., 44, 4877-4880.
24. Lemay, M. and Ogilvie, W.W. (2005) Org. Lett., 7, 4141-4144 .
25. Wilson, R.M., Jen, W.S., and MacMillan, D.W.C. (2005) J. Am. Chem. Soc., 127, 11616-11617.
26. Kano, T., Tanaka, Y., and Maruoka, K. (2006) Org. Lett., 8, 2687-2689.
27. He, M., Struble, J.R., and Bode, J.W. (2006) J. Am. Chem. Soc., 128, 8418-8420.
28. Nakashima, D. and Yamamoto, H. (2006) J. Am. Chem. Soc., 128, 9626-9627.
29. Goto, H. and Hayashi, J. (2007) Org. Lett., 9, 2859 - 2862;
30. For a review, see: (l) Merino, P., Marqués-López, E., Tejero, T., and Herrera, R.P. (2010) Synthesis, 1-26.
31. Bui, T. and Barbas, C.F. III (2000) Tetrahedron Lett., 41, 6951-6954.
32. List, B., Pojarliev, P., and Martin, J. (2001) Org. Lett., 3, 2423-2425.
33. Betancort, J.M. and Barbas, C.F. III (2001) Org. Lett., 3, 3737-3740.
34. Hallan, N., Aburel, P.S., and Jørgensen, K.A. (2004) Angew. Chem., Int. Ed., 43, 1272-1277
35. For recent reviews, see: (e) Tsogoeva, S.B. (2007) Eur. J. Org. Chem., 1701-1716.
36. Vicario, J.L., Badía, D., and Carillo, L. (2007) Synthesis, 2065-2092.
37. Almasi, D., Alonso, D.A., and Nájera, C. (2007) Tetrahedron: Asymmetry, 18, 299-365 .
38. Enders, D., Wang, C., and Liebich, J.X. (2009) Chem. Eur. J., 15, 11058 - 11076.
39. Roca-López, D., Sadaba, D., Delso, I., Herrera, R., Tejero, T., and Merino, P. (2010) Tetrahedron: Asymmetry, 21, 2561-2601.
40. Dondoni, A. and Massi, A. (2008) Angew. Chem., Int. Ed., 47, 4638-4660.
41. Melchiorre, P., Marigo, M., Carlone, A., and Bartoli, G. (2008) Angew. Chem., Int. Ed., 47, 6138-6171.
42. Bertelsen, S. and Jørgensen, K.A. (2009) Chem. Soc. Rev., 38, 2178-2189.
43. Bartoli, G. and Melchiorre, P. (2008) Synlett, 1759-1772 .
44. Connon, S.J. (2007) Org. Biol. Chem., 5, 3407-3417.
45. Yu, X. and Wang, W. (2008) Chem. Asian J., 3, 516-532 .
46. Gruttadauria, M., Giacalone, F., and Noto, R. (2009) Adv. Synth. Catal., 351, 33-57.
47. Peng, F., and Shao, Z. (2008) J. Mol. Catal. A, 285, 1-13.
48. Werner, T. (2009) Adv. Synth. Catal., 351, 1469-1481 .
49. Paradowska, J., Stodulski, M., and Mlynarski, J. (2009) Angew. Chem., Int. Ed., 48, 4288-4297.
50. Toma, S., Meciarová, M., and Sebesta, R. (2009) Eur. J. Org. Chem., 321-327.
51. Liu, X., Lin, L., and Feng, X. (2009) Chem. Commun., 6145-6158.
52. Bella, M. and Gasperi, T. (2009) Synthesis, 1583-1614 .
53. Valero, G., Companyó, X., Bravo, N., Alba, A.-N.R., Moyano, A., and Rios, R. (2010) Synlett, 1883-1908;
54. Marcelli, T. and Hiemstra, H. (2010) Synthesis, 1229-1279.
55. Müller, C.E. and Schreiner, P.R. (2011) Angew. Chem., Int. Ed., 50, 6012-6042.
56. Albrecht, L., Jiang, H., and Jørgensen, K.A. (2011) Angew. Chem., Int. Ed., 50, 8492-8509 .
57. Pellissier, H. (2011) Adv. Synth. Catal., 353, 659-676.
58. Moyano, A. and Rios, R. (2011) Chem. Rev., 111, 4703-4832.
59. Moyano, A., El-Hamdouni, N., and Atlamsani, A. (2010) Chem. Eur. J., 16, 5260-5273.
60. Steglich, W. and Höfl e, G. (1969) Chem. Ber., 102, 883-898.
61. Steglich, W. and Höfl e, G. (1970) Tetrahedron Lett., 11, 4729-4730.
62. Ruble, J.C. and Fu, G.C. (1998) J. Am. Chem. Soc., 120, 11532-11533.
63. Fu, G.C. (2000) Acc. Chem. Res., 33, 412-420.
64. Fu, G.C. (2004) Acc. Chem. Res., 37, 542-547.
65. Hills, I.D. and Fu, G.C. (2003) Angew. Chem., Int. Ed., 42, 3921-3924.
66. The racemic version of this rearrangement had been previously reported by Black et al.: Black, T.H., Arrivo, S.M., Schumm, J.S., and Knobeloch, J.M. (1986) J. Chem. Soc., Chem. Commun., 1524-1525.
67. Black, T.H., Arrivo, S.M., Schumm, J.S., and Knobeloch, J.M. (1987) J. Org. Chem., 59, 5425-5430.
68. Nguyen, H.V., Butler, D.C., and Richards, C.J. (2006) Org. Lett., 8, 769-772.
69. Ismail, M., Nguyen, H.V., Ilyashenko, G., Motevali, M., and Richards, C.J. (2009) Tetrahedron Lett., 50, 6332-6334.
70. Seitzberg, J.G., Dissing, C., Søtofte, I., Morrby, P.-O., and Johanssen, M. (2005) J. Org. Chem., 70, 8332-8337.
71. Busto, E., Gotor-Fernández, V., and Gotor, V. (2006) Adv. Synth. Catal., 348, 2626-2632.
72. Preliminary communication: Shaw, S.A., Aleman, P., and Vedejs, E. (2003) J. Am. Chem. Soc., 125, 13368-13369;
73. Full paper: (b) Shaw, S.A., Aleman, P., Christy, J., Kampf, J.W., Va, P., and Vedejs, E. (2006) J. Am. Chem. Soc., 128, 925-934.
74. For the competition between C4 and C2 in the organocatalytic Michael additions of oxazolones, see: Balaguer, A.-N., Companyó, X., Calvet, T., Font-Bardía, M., Moyano, A., and Rios, R. (2009) Eur. J. Org. Chem., 199-203.
75. Alba, A.-N.R., Valero, G., Calvet, T., Font-Bardía, M., Moyano, A., and Rios, R. (2012) New J. Chem., 36, 613-618.
76. Duffey, T.A., Shaw, S.A., and Vedejs, E. (2009) J. Am. Chem. Soc., 131, 14-15.
77. Dietz, F.R. and Gröger, H. (2008) Synlett, 663-666.
78. Dietz, F.R. and Gröger, H. (2009) Synthesis, 4208-4218.
79. Birman, V.B. and Li, X. (2008) Org. Lett., 10, 1115-1118.
80. Joannesse, C., Johnston, C.P., Concellón, C., Simal, C., Philp, D., and Smith, A.D. (2009) Angew. Chem., Int. Ed., 48, 8914-8918.
81. Joannesse, C., Morril, L.C., Campbell, C.D., Slavin, A.M.Z., and Smith, A.D. (2011) Synthesis, 1865-1879.
82. Viswambharan, B., Okimura, T., Suzuki, S., and Okamoto, S. (2011) J. Org. Chem., 76, 6678-6685.
83. Zhang, Z., Xie, F., Jia, J., and Zhang, W. (2010) J. Am. Chem. Soc., 132, 15939-15941.
84. Thomson, J.E., Kyle, A.F., Gallagher, K.A., Lenden, P., Concellón, C., Morrill, L.C., Miller, A.J., Joannesse, C., Slawin, A.M.Z., and Smith, A.D. (2008) Synthesis, 2805-2818.
85. Campbell, C.D., Concellón, C., and Smith, A.D. (2011) Tetrahedron: Asymmetry, 22, 797-811.
86. Uraguchi, D., Koshimoto, K., Miyake, S., and Ooi, T. (2010) Angew. Chem., Int. Ed., 49, 5567-5569.
87. De, C.K., Mittal, N., and Seidel, D. (2011) J. Am. Chem. Soc., 133, 16802-16805.
88. Kobbelgaard, S., Brandes, S., and Jørgensen, K.A. (2008) Chem. Eur. J., 14, 1464-1471.
89. Reviews: Hollis, T.K. and Overman, L.E. (1999) J. Organomet. Chem., 576, 290-299.
90. Overman, L.E. and Carpenter, N.E. (2005) Org. React., 66, 1-107.
91. Majumdar, K.C., Bhattacharyya, T., Chattopadhyay, B., and Sinha, B. (2009) Synthesis, 2117-2142 ;
92. Recent references: (d) Anderson, C.E. and Overman, L.E. (2003) J. Am. Chem. Soc., 125, 12412-12413.
93. Moyano, A., Rosol, M., Moreno, R.M., López, C., and Maestro, M.A. (2005) Angew. Chem., Int. Ed., 44, 1865-1869.
94. Weiss, M.E., Fischer, D.F., Xin, Z., Jautze, S., Schweizer, W.B., and Peters, R. (2006) Angew. Chem., Int. Ed., 45, 5694-5698 .
95. Nomura, H. and Richards, C.J. (2007) Chem. Eur. J., 13, 10216-10224.
96. Watson, M.P., Overman, L.E., and Bergman, R.G. (2007) J. Am. Chem. Soc., 129, 5031-5044.
97. Jautze, S., Seiler, P., and Peters, R. (2007) Angew. Chem., Int. Ed., 46, 1260-1264.
98. Swift, M.D. and Sutherland, A. (2007) Org. Lett., 9, 5239-5242.
99. Jautze, S., Seiler, P., and Peters, R. (2008) Chem. Eur. J., 14, 1430-1444.
100. Xin, Z., Fischer, D.F., and Peters, R. (2008) Synlett, 1495-1499.
101. Fischer, D.F., Barakat, A., Xin, Z., Weiss, M.E., and Peters, R. (2009) Chem. Eur. J., 15, 8722-8741.
102. Liu, H., Leow, D., Huang, K.-W., and Tan, C.-H. (2009) J. Am. Chem. Soc., 131, 7212-7213.
103. Huang, D., Qin, S., and Hu, C. (2011) Org. Biomol. Chem., 9, 6034-6039.
104. Wu, Y., Singh, R., and Deng, L. (2011) J. Am. Chem. Soc., 133, 12458-12461.
105. Capitta, F., Frongia, A., Piras, P., Pitzanti, P., and Secci, F. (2010) Adv. Synth. Catal., 352, 2955-2960.
106. Capitta, F., Frongia, A., Piras, P., Pitzanti, P., and Secci, F. (2012) Org. Biomol. Chem., 10, 490-494.
107. Hodgson, D.M., Pierard, F.Y.T.M., and Stapple, P.A. (2001) Chem. Soc. Rev., 30, 50-61.
108. McNally, A., Evans, B., and Gaunt, M.J. (2006) Angew. Chem., Int. Ed., 45, 2116-2119.
109. For the highly enantioselective rearrangement of ester-substituted allyl vinyl ethers catalyzed by copper(II) bisoxazoline complexes, see: Abraham, L., Czerwonka, R., and Hiersemann, M. (2001) Angew. Chem., Int. Ed., 40, 4700-4703.
110. Abraham, L., Körner, M., Schwab, P., and Hiersemann, M. (2004) Adv. Synth. Catal., 346, 1281-1294.
111. Severance, D.L. and Jorgensen, W.L. (1992) J. Am. Chem. Soc., 114, 10966-10968.
112. Curran, D. and Kuo, L.H. (1995) Tetrahedron Lett., 36, 6647-6650.
113. Kirsten, M., Rehbein, J., and Hiersemann, M. (2007) J. Org. Chem., 72, 4001-4011.
114. Uyeda, C. and Jacobsen, E.N. (2008) J. Am. Chem. Soc., 130, 9228-9229.
115. Uyeda, C. and Jacobsen, E.N. (2011) J. Am. Chem. Soc., 133, 5062-5075.
116. Uyeda, C., Rötheli, A.R., and Jacobsen, E.N. (2010) Angew. Chem., Int. Ed., 49, 9753-9756.
117. Kaeobamrung, J., Mahatthananchai, J., Zhang, P., and Bode, J.W. (2010) J. Am. Chem. Soc., 132, 8810-8812.
118. Coates, R.M., Shah, S.K., and Mason, R.W. (1982) J. Am. Chem. Soc., 104, 2198-2208.
119. Coates, R.M. and Hobbes, S.J. (1984) J. Org. Chem., 49, 140-152 .
120. Coates, R.M., Rogers, B.D., Hobbes, S.J., Peck, D.R., and Curran, D.P. (1987) J. Am. Chem. Soc., 109, 1160-1170.
121. Chow, Y.-K. and Bode, J.W. (2004) J. Am. Chem. Soc., 126, 8126-8127.
122. Reynolds, N.T., Read de Alaniz, J., and Rovis, T. (2004) J. Am. Chem. Soc., 126, 9518-9519.
123. Sohn, S.S. and Bode, J.W. (2005) Org. Lett., 7, 3873-3876.
124. Zeitler, K. (2006) Org. Lett., 8, 637-640.
125. Wanner, B., Mahatthananchai, J., and Bode, J.W. (2011) Org. Lett., 13, 5378-5381.
126. Rueping, M. and Antonchick, A.K. (2008) Angew. Chem., Int. Ed., 47, 10090-10093.
127. Horowitz, R.M. and Geissman, T.A. (1950) J. Am. Chem. Soc., 72, 1518-1522.
128. Ren, H. and Wulff, W.D. (2011) J. Am. Chem. Soc., 133, 5656-5659.
129. Frauenrath, H., Arenz, T., Raabe, G., and Zorn, M. (1993) Angew. Chem., Int. Ed. Engl., 32, 83-85.
130. Arenz, T., Frauenrath, H., Raabe, G., and Zorn, M. (1994) Liebigs Ann. Chem., 931-942 .
131. Tayama, E., Otoyama, S., and Isaka, W. (2008) Chem. Commun., 4216-4218.
132. Terada, M. and Toda, Y. (2009) J. Am. Chem. Soc., 131, 6354-6355.
133. List, B., Pojarliev, P., Biller, W.T., and Martin, H.J. (2002) J. Am. Chem. Soc., 124, 827-833.
134. Córdova, A. (2003) Synlett, 1651-1654.
135. Hayashi, Y., Tsuboi, W., Ashimine, I., Urushima, T., Shoji, M., and Sakai, K. (2003) Angew. Chem., Int. Ed., 42, 3677-3680.
136. Notz, W., Tanaka, F., Watanabe, S., Chowdari, N.S., Turner, J.M., Thayumanavan, R., and Barbas, C.F. III (2003) J. Org. Chem., 68, 9624-9634;
137. For other organocatalytic approaches to anti-Mannich adducts, see: (e) Kano, T., Yamaguchi, Y., Tokuda, O., and Maruoka, K. (2005) J. Am. Chem. Soc., 127, 16408-11409.
138. Franzén, J., Marigo, M., Fielenbach, D., Wabnitz, T.C., Kjaersgaard, A., and Jørgensen, K.A. (2005) J. Am. Chem. Soc., 127, 18296 - 18304.
139. Mitsumori, S., Zhang, H., Cheong, P.H.-Y., Houk, K.N., Tanaka, F., and Barbas, C.F. III (2006) J. Am. Chem. Soc., 128, 1040-1041.
140. Zhang, E., Fan, C.-A., Tu, Y.-Q., Zhang, F.-M., and Song, Y.-L. (2009) J. Am. Chem. Soc., 131, 14626-14627.
141. Zhang, Q.-W., Fan, C.-A., Zhang, H.-J., Tu, Y.-Q., Zhao, Y.-M., Gu, P., and Chen, Z.-M. (2009) Angew. Chem., Int. Ed., 48, 8572-8574.
142. Li, B.-S., Zhang, E., Zhang, Q.-W., Zhang, F.-M., Tu, Y.-Q., and Cao, X.-P. (2011) Chem. Asian J., 6, 2269-2272.
143. Wang, X., Reisinger, C.M., and List, B. (2008) J. Am. Chem. Soc., 130, 6070-6071.
144. Chen, Z.-M., Zhang, Q.-W., Chen, Z.-H., Li, H., Tu, Y.-Q., Zhang, F.-M., and Tian, J.-M. (2011) J. Am. Chem. Soc., 133, 8818-8821.
145. Müller, C.H., Wilking, M., Rühlmann, A., Wibbeling, B., and Hennecke, U. (2011) Synlett, 2043-2047.
146. Yang, L., Liu, R.-H., Wang, B., Weng, L.-L., and Zheng, H. (2009) Tetrahedron Lett., 50, 2628-2631.
147. Capitta, F., Frongia, A., Olivier, J., Piras, P., and Secci, F. (2011) Synlett, 89-93 .
148. Quintard, A. and Alexakis, A. (2009) Chem. Eur. J., 15, 11109-11113 .
149. Quintard, A. and Alexakis, A. (2011) Org. Biomol. Chem., 9, 1407-1418 .
150. Bravo, N., Alba, A.-N., Valero, G., Companyó, X., Moyano, A., and Rios, R. (2010) New J. Chem., 34, 1816-1820 .
151. Holub, N., Jiang, H., Paixão, M.W., Tiberi, C., and Jørgensen, K.A. (2010) Chem. Eur. J., 16, 4337-4346;
152. For the racemic organocatalytic rearrangement of pyranones followed by enzymatic kinetic resolution, see: (g) Caddick, S., Cheung, S., Doyle, V.E., Frost, L.M., Soscia, M.G., Delisser, V.M., Williams, M.R.V., Etheridge, Z.C., Khan, S., Hitchcock, P.B., Pairaudeau, G., and Vile, S. (2001) Tetrahedron, 57, 6295-6303.
153. Nunes, J.P.M., Afonso, C.A.M., and Caddick, S. (2009) Tetrahedron Lett., 50, 3706-3708 .
154. Nunes, J.P.M., Veiros, L.F., Vaz, P.D., Afonso, C.A.M., and Caddick, S. (2011) Tetrahedron, 67, 2779-2787.
155. Liang, T., Zhang, Z., and Antilla, J.C. (2010) Angew. Chem., Int. Ed., 49, 9734-9736.