An unexpected michael-aldol-Smiles rearrangement sequence for the synthesis of versatile optically active bicyclic structures by using asymmetric organocatalysis

Chemistry - A European Journal

Volumn 16, Issue 14, 2010, Pages 4337-4346

  Holub, Nicole ^a   Jiang, Hao ^a   Paixão, Mareio W ^a   Tiberi, Caterina ^a   Jørgensen, Karl A ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Asymmetric catalysis; Bicycles; Enones; Organocatalysis; Smiles rearrangement

Indexed keywords

ASYMMETRIC CATALYSIS; BICYCLIC STRUCTURE; COPE REARRANGEMENT; CYCLIC KETONES; CYCLISATIONS; INTRAMOLECULAR ALDOL REACTIONS; MECHANISTIC PATHWAYS; NATURAL PRODUCTS; OPTICALLY ACTIVE; ORGANOCATALYSIS; ORGANOCATALYTIC; RING-EXPANDING REACTIONS; SMILES REARRANGEMENT; STEREO-SELECTIVE; TRIFLUOROACETIC ACIDS;

BICYCLES; FREE RADICAL REACTIONS; HYDROCARBONS; KETONES; PHOTOCHEMICAL REACTIONS; RATE CONSTANTS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CATALYSIS;

EID: 77950835043     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903274     Document Type: Article

References (142)

1. a) A. Srikrishna, S. Danieldoss, Synth. Commun. 1997, 27, 655;
2. b) M.-S. Yang, S.-S. Lu, C. P. Rao, Y.-F. Tsai, C.-C. Liao, J. Org. Chem. 2003, 68, 6543;
3. c) G. Gescheidt, D. Neshchadin, G. Rist, A. Borer, K. Dietliker, K. Misteli, Phys. Chem. Chem. Phys. 2003, 5, 1071;
4. d) S. Banerjee, S. Yadav, S. Lahiri, Org. Lett. 2009, 11, 3494.
5. a) A. Srikrishna, G. V. R. Sharma, P. Hemamalini, J. Chem. Soc. Chem. Commun. 1990, 1681;
6. b) A. Srikrishna, P. Hemamalini, G. V. R. Sharma, J. Org. Chem. 1993, 58, 2509;
7. c) N.-C. Chang, C.-K. Chang, J. Org. Chem. 1996, 61, 4967;
8. d) A. Srikrishna, D. Vijaykumar, G. V. R. Sharma, Tetrahedron Lett. 1997, 38, 2003;
9. e) A. Srikrishna, S. Danieldoss, J. Org. Chem. 1997, 62, 7863;
10. f) V. Singh, S. Pal, S. M. Mobin, J. Org. Chem. 2006, 71, 3014.
11. For reviews about diene-ligands, see: a) T. Hayashi, Synlett 2001, 0879;
12. b) T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103-103, 2829;
13. c) T. Hayashi, Shokubai 2005, 47, 533;
14. d) C. Defieber, H. Grutzmacher, E. M. Carreira, Angew. Chem. 2008, 120, 4558;
15. Angew. Chem. Int. Ed. 2008, 47, 4482;
16. for the application of diene ligands in Rh-catalysed 1,4-additions, see for example: e) C. Defieber, J.-F. Paquin, S. Serna, E. M. Carreira, Org. Lett. 2004, 6, 3873;
17. f) C. Fischer, C. Defieber, T. Suzuki, E. M. Carreira, J. Am. Chem. Soc. 2004, 126, 1628;
18. g) J.-F. Paquin, C. Defieber, C. R. J. Stephenson, E. M. Carreira, J. Am. Chem. Soc. 2005, 127, 10850;
19. h) J.-F. Paquin, C. R. J. Stephenson, C. Defieber, E. M. Carreira, Org. Lett. 2005, 7, 3821;
20. i) T. C. Fessard, S. P. Andrews, H. Motoyoshi, E. M. Carreira, Angew. Chem. 2007, 119, 9492;
21. Angew. Chem. Int. Ed. 2007, 46, 9331;
22. j) T. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida, J. Am. Chem. Soc. 2003, 125, 11508;
23. k) N. Tokunaga, Y. Otomaru, K. Okamoto, K. Ueyama, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2004, 126, 13584;
24. l) Y. Otomaru, N. Tokunaga, R. Shintani, T. Hayashi, Org. Lett. 2005, 7, 307;
25. m) Y. Otomaru, K. Okamoto, R. Shintani, T. Hayashi, J. Org. Chem. 2005, 70, 2503;
26. n) Y. Otomaru, A. Kina, R. Shintani, T. Hayashi, Tetrahedron: Asymmetry 2005, 16, 1673;
27. o) T. Nishimura, H. Kumamoto, M. Nagaosa, T. Hayashi, Chem. Commun. 2009, 5713;
28. p) R. Shintani, Y. Tsutsumi, M. Nagaosa, T. Nishimura, T. Hayashi, J. Am. Chem. Soc. 2009, 131, 13588;
29. q) K. Okamoto, T. Hayashi, V. H. Rawal, Chem. Commun. 2009, 4815.
30. For examples of total syntheses, see: a) B. B. Snider, Z. Chen, Org. Prep. Proced. 1999, 31, 537;
31. b) S. Dong, E. Hamel, R. Bai, D. G. Covell, J. A. Beutler, J. A. Porco, Jr., Angew. Chem. 2009, 121, 1522;
32. Angew. Chem. Int. Ed. 2009, 48, 1494;
33. for the isolation of the natural products, see: c) K. Yueh-Hsuing, C. Chia-Hsien, H. Shou-Ling, Chem. Pharm. Bull. 1998, 46, 181;
34. d) K. Yueh-Hsuing, C. Chia-Hsien, C. Shih-Chang, L. Hsiu-Chuan, Chem. Pharm. Bull. 2004, 52, 764;
35. e) C. Shih-Chang, C. Jang-Yang, K. Ching-Chuan, H. Cheng-Chih, Y. Ning-Sun, K. Yueh-Hsiung, Tetrahedron Lett. 2007, 48, 1567.
36. a) D. A. Evans, A. M. Golob, J. Am. Chem. Soc. 1975, 97, 4765;
37. b) C.-H. Chen, R. K. Peddenti, N. S. Kameswara Rao, C.-C. Liao, J. Org. Chem. 2004, 69, 5365;
38. c) D.-S. Hsu, P.-Y. Hsu, Y.-C. Lee, C.-C. Liao, J. Org. Chem. 2008, 73, 2554.
39. a) M.-S. Yang, S.-Y. Chang, S.-S. Lu, P. D. Rao, C.-C. Liao, Synlett 1999, 225;
40. b) Y.-S. Lin, S.-Y. Chang, M.-S. Yang, C. P. Rao, R. K. Peddinti, Y.-F. Tsai, C.-C. Liao, J. Org. Chem. 2004, 69, 447;
41. c) V. Singh, G. D. Praveena, S. M. Mobin, Tetrahedron 2004, 60, 4177;
42. d) V. Singh, P. K. Sahu, B. C. Sahu, S. M. Mobin, J. Org. Chem. 2009, 74, 6092;
43. for a chiral synthesis, using auxiliaries, see: S.-Y. Luo, Y.-J. Jang, J.-Y. Liu, C.-S. Chu, C.-C. Liao, S.-C. Hung, Angew. Chem. 2008, 120, 8202;
44. Angew. Chem. Int. Ed. 2008, 47, 8082.
45. M. Murakami, S. Ashida, Chem. Commun. 2006, 4599.
46. A. Srikrishna, G. V. R. Sharma, S. Danieldoss, P. Hemamalini, J. Chem. Soc. Perkin Trans. 1 1996, 1305.
47. M. E. Jung, A. Maderna, Tetrahedron Lett. 2005, 46, 5057.
48. For recent reviews on organocatalysis, see: a) M. J. Gaunt, C. C. Johansson, A. McNally, N. C. Vo, Drug Discovery Today 2007, 12, 8;
49. b) P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232;
50. Angew. Chem. Int. Ed. 2008, 47, 6138;
51. c) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716;
52. Angew. Chem. Int. Ed. 2008, 47, 4638;
53. d) Chem. Rev. 2007, 107(12),
54. special issue on organocatalysis; e) S. Bertelsen, K. A. Jargensen, Chem. Soc. Rev. 2009, 38, 2178;
55. f) D. W. C. MacMillan, Nature 2008, 455, 304;
56. g) C. F. Barbas III, Angew. Chem. 2007, 119, 44;
57. Angew. Chem. Int. Ed. 2007, 47, 42;
58. h) A. Mielgo, C. Palomo, Chem. Asian J. 2008, 3, 922;
59. i) A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416;
60. j) B. List, Chem. Commun. 2006, 819.
61. a) Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5962;
62. b) H. Sundén, I. Ibrahem, L. Eriksson, A. Córdova, Angew. Chem. 2005, 117, 4955;
63. Angew. Chem. Int. Ed. 2005, 44, 4877;
64. c) R. M. Wilson, S. Wendey, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 11616;
65. d) T. Kano, Y. Tanaka, K. Maruoka, Org. Lett. 2006, 8, 2687;
66. e) H. Gotoh, Y. Hayashi, Org. Lett. 2007, 9, 2859;
67. f) N. Momiyama, Y. Yamamoto, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 1190;
68. g) J. Payette, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 9536;
69. h) B. Han, L. Z.-Q. He, J.-L. Li, R. Li, K. Jiang, T.-Y. Liu, Y.-C. Chen, Angew. Chem. 2009, 121, 5582;
70. Angew. Chem. Int. Ed. 2009, 48, 5474;
71. i) M. Bella, D. M. S. Schietroma, P. P. Cusella, T. Gasperi, V. Visca, Chem. Commun. 2009, 597;
72. j) H. Yang, R. G. Carter, J. Org. Chem. 2009, 74, 5151;
73. k) D.-Q. Xu, A.-B. Xia, S.-P. Luo, J. Tang, S. Zhang, J.-R. Jiang, Z.-Y. Xu, Angew. Chem. 2009, 121, 3879;
74. Angew. Chem. Int. Ed. 2009, 48, 3821;
75. l) J. Y.-T. Soh, C.-H. Tan, J. Am. Chem. Soc. 2009, 131, 6904;
76. m) C.-L. Cao, Y.-Y. Zhou, J. Zhou, X.-L. Sun, Y. Tang, Y.-X. Li, G.-Y. Li, J. Sun, Chem. Eur. J. 2010, 15, 11384.
77. For selected publications, see: a) J.-W. Xei, 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;
78. Angew. Chem. Int. Ed. 2007, 46, 389;
79. b) G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403;
80. c) X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2008, 130, 6070;
81. d) J. Zhou, V. Wakchaure, P. Kraft, B. List, Angew. Chem. 2008, 120, 7768;
82. Angew. Chem. Int. Ed. 2008, 47, 7656;
83. e) C.M. Reisinger, X. Wang, B. List, Angew. Chem. 2008, 120, 8232;
84. Angew. Chem. Int. Ed. 2008, 47, 8112;
85. f) X. Lu, Y. Liu, B. Sun, B. Cindric, L. Deng, J. Am. Chem. Soc. 2008, 130, 8134;
86. g) F. Pesciaioli, F. D. Vincentiis, P. Galzerano, G. Bencivenni, G. Bartoli, A. Mazzanti, P. Melchiorre, Angew. Chem. 2008, 120, 8831;
87. Angew. Chem. Int. Ed. 2008, 47, 8703;
88. h) X. Lu, L. Deng, Angew. Chem. 2008, 120, 7824;
89. Angew. Chem. Int. Ed. 2008, 47, 7710;
90. i) B. Tan, P. J. Chua, X. Zeng, M. Lu, G. Zhong, Org. Lett. 2008, 10, 3489;
91. j) B. Tan, Z. Shi, P. J. Chua, G. Zhong, Org. Lett. 2008, 10, 3425;
92. k) B. Tan, P. J. Chua, Y. Li, G. Zhong, Org. Lett. 2008, 10, 2437;
93. l) G. Bartoli, P. Melchiorre, Synlett 2008, 1759;
94. m) B. Tan, X. Zhang, P. J. Chua, G. Zhong, Chem. Commun. 2009, 779.
95. a) M. W. Paixão, N. Holub, C. Vila, M. Nielsen, K. A. Jørgensen, Angew. Chem. 2009, 121, 7474;
96. Angew. Chem. Int. Ed. 2009, 48, 7338;
97. b) M. Nielsen, C. B. Jacobsen, M. W. Paixão, N. Holub, K. A. Jørgensen, J. Am. Chem. Soc. 2009, 131, 10581.
98. For selected examples of asymmetric organocatalysed 1,4-additions to enones, see: a) N. Halland, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2002, 67, 8331;
99. b) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685;
100. Angew. Chem. Int. Ed. 2003, 42, 661;
101. c) B. Vakulya, S. Varga, A. Csampai, T. Soos, Org. Lett. 2005, 7, 1967;
102. d) C. E. T. Mitchell, S. E. Brenner, S. V. Ley, Chem. Commun. 2005, 5346;
103. e) K. R. Knudsen, C. E. T. Mitchell, S. V. Ley, Chem. Commun. 2006, 66;
104. f) D.-P. Li, Y.-C. Guo, Y. Ding, W.-J. Xiao, Chem. Commun. 2006, 799;
105. g) C. E. T. Mitchell, S. E. Brenner, J. Garcia-Fortanet, S. V. Ley, Org. Biomol. Chem. 2006, 4, 2039;
106. h) M. Malmgren, J. Granander, M. Amedjkouh, Tetrahedron: Asymmetry 2008, 19, 1934;
107. Y.-Q. Yang, G. Zhao, Chem. Eur. J. 2008, 14, 10888;
108. j) F. Pesciaioli, F. De Vincentiis, P. Galzerano, G. Bencivenni, G, Bartoli, A. Mazzanti, P. Melchiorre, Angew. Chem. 2008, 120, 8831;
109. Angew. Chem. Int. Ed. 2008, 47, 8703;
110. k) X.-J. Lu, Y. Liu, B.-F. Sun, B. Cindric, Li Deng, J. Am. Chem. Soc. 2008, 130, 8134;
111. l) C. M. Reisinger, X.-W. Wang, B. List, Angew. Chem. 2008, 120, 8232;
112. Angew. Chem. Int. Ed. 2008, 47, 8112;
113. m) J. Lv, J. Zhang, Z. Lin, Y. Wang, Chem. Eur. J. 2009, 15, 972;
114. n) S. Sulzer-Mossé, A. Alexakis, J. Mareda, G. Bollot, G. Bernardinelli, Y. Filinchuk, Chem. Eur. J. 2009, 15, 3204;
115. o) G. Luo, S. Zhang, W. Duan, W. Wang, Synthesis 2009, 1564;
116. p) K. Mei, M. Jin, S. Zhang, P. Li, W. Liu, X. Chen, F. Xue, W. Duan, W. Wang, Org. Lett. 2009, 11, 2864;
117. q) E. Riguet, Tetrahedron Lett. 2009, 50, 4283.
118. a) L. A. Warren, S. Smiles, J. Chem. Soc. 1930, 1327;
119. for examples of the Julia-Kocienski reaction employing the Smiles rearrangement, see: b) P. R. Blakemore, W. J. Cole, P. J. Kocienski, A. Morley, Synlett 1998, 26;
120. c) J. B. Baudin, G. Hareau, S. A. Julia, Tetrahedron Lett. 1991, 32, 1175;
121. d) P. R. Blakemore, J. Chem. Soc. Perkin Trans. 1 2002, 2563;
122. e) C. Aissa, Eur. J. Org. Chem. 2009, 1831.
123. Selected examples of asymmetric catalytic processes that result in low enantio-selectivities for application to cyclopentenone as a substrate, see: a) M. Shi, X.-G. Liu, Org. Lett. 2008, 10, 1043;
124. b) X. Wang, C. Reisinger, B. List, J. Am. Chem. Soc. 2008, 130, 6070;
125. c) P. Li, Y. Wang, X. Liang, J. Xe, Chem. Commun. 2008, 3302;
126. d) P. Li, S. Wen, F. Yu, Q. Liu, W. Li, Y. Wang, X. Liang, J. Ye, Org. Lett. 2009, 11, 753;
127. e) T. Nishimura, S. Tokuji, T. Sawano, T. Hayashi, Org. Lett. 2009, 11, 3222.
128. L. Finet, M. Dakir, I. Castellote, S. Arseniyadis, Eur. J. Org. Chem. 2007, 4116.
129. a) E. Nyfeler, P. Renaud, Chimia 2006, 60, 276;
130. b) L. Kürti, B. Czáko, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier, Amsterdam, 2005, p. 396.
131. For a recent review about RRM, see: a) N. Holub, S. Blechert, Chem. Asian J. 2007, 2, 1064;
132. for applications of bicyclooctenes in RRM, see for example: b) T. L. Minger, A. J. Phillips, Tetrahedron Lett. 2002, 43, 5357;
133. c) M. W. B. Pfeiffer, A. J. Phillips, J. Am. Chem. Soc. 2005, 127, 5334;
134. for recent reviews about ROMP, see: d) M. Buchmeiser, Chim. Oggi 2007, 25, 78;
135. e) C. W. Bielawski, R. H. Grubbs, Prog. Polym. Sci. 2007, 32, 1;
136. for examples applying bicyclooctenes in ROMP processes, see: f) V. P. Conticello, D. L. Gin, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 9708;
137. g) J. G. Hamilton, K. J. Ivin, J. J. Rooney, Br. Polym. J. 1985, 17, 41;
138. for a review about ROM/CM, see for example: h) O. Arjona, A. G. Csákÿ, J. Plumet, Synthesis 2000, 857.
139. a) I. Sarvary, F. Almqvist, T. Frejd, Chem. Eur. J. 2001, 7, 2158;
140. b) I. Sarvary, P. Norrby, T. Frejd, Chem. Eur. J. 2004, 10, 182;
141. c) A. Friberg, I. Sarvary, O. F. Wendet, T. Frejd, Tetrahedron: Asymmetry 2008, 19, 1765;
142. d) C. Olsson, A. Friberg, T. Frejd, Tetrahedron: Asymmetry 2008, 19, 1476.