Bifunctional squaramide catalysts with the same absolute chirality for the diastereodivergent access to densely functionalised cyclohexanes through enantioselective domino reactions. Synthesis and mechanistic studies

Advanced Synthesis and Catalysis

Volumn 356, Issue 17, 2014, Pages 3627-3648

  Martínez, Jose I ^a   Villar, Laura ^a   Uria, Uxue ^a   Carrillo, Luisa ^a   Reyes, Efraím ^a   Vicario, Jose L ^a  

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

Author keywords

Asymmetric catalysis; Domino reactions; Hydrogen bonds; Organocatalysis; Reaction mechanism

Indexed keywords

EID: 84915745696     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400502     Document Type: Article

References (124)

1. J. Muzart, Tetrahedron 2013, 69, 6735
2. H. Pellissier, Chem. Rev. 2013, 113, 442
3. C. J. Ball, M. C. Willis, Eur. J. Org. Chem. 2013, 425
4. E. Ricca, B. Brucher, J. H. Schrittwieser, Adv. Synth. Catal. 2011, 353, 2239
5. E. A. Anderson, Org. Biomol. Chem. 2011, 9, 3997
6. T. Vlaar, E. Ruijter, R. V. A. Orru, Adv. Synth. Catal. 2011, 353, 809
7. K. C. Nicolaou, J. S. Chen, Chem. Soc. Rev. 2009, 38, 2993
8. J Barluenga F. Rodriguez, F. J. FaCanas Chem. Asian J. 2009, 4, 1036
9. B. B. Toure, D. G. Hall, Chem. Rev. 2009, 109, 4439
10. N. Ismabery, R. Lavila, Chem. Eur. J. 2008, 14, 8444
11. B. Albert, K. Scott, Tetrahedron 2007, 63, 5341
12. C. J. Chapman, C. G. Frost, Synthesis 2007, 1
13. H. Miyabe, Y. Takemoto, Chem. Eur. J. 2007, 13, 7280
14. N. T. Patil, Y. Yamamoto, Synlett 2007, 994
15. D. Tejedor, F. Garcia-Tellado, Chem. Soc. Rev. 2007, 36, 484
16. A. Padwa, S. K. Bur, Tetrahedron 2007, 63, 5341
17. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292
18. Angew. Chem. Int. Ed. 2006, 45, 7134
19. A. Doemling, Chem. Rev. 2006, 106, 17
20. H.-C. Guo, J.-A. Ma, Angew. Chem. 2006, 118, 362
21. Angew. Chem. Int. Ed. 2006, 45, 354
22. D. J. Ramon, M. Yus, Angew. Chem. 2005, 117, 1628
23. Angew. Chem. Int. Ed. 2005, 44, 1602
24. J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001.
25. Z. Galestokova, R. Sebesta, Eur. J. Org. Chem. 2012, 6688
26. M. Ruiz, P. Lopez-Alvarado, G. Giorgi, J. C. Menendez, Chem. Soc. Rev. 2011, 40, 3445
27. D. Bonne, Y. Coquerel, T. Constantieux, J. Rodriguez, Tetrahedron: Asymmetry 2010, 21, 1085
28. H. Lebel, J. F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977
29. D. Caine, Tetrahedron 2001, 57, 2643
30. G. Balme, D. Bouyssi, N. Monteiro, Top. Organomet. Chem. 2006, 19, 115.
31. Y. Sohtome, K. Nagasawa, Org. Biomol. Chem. 2014, 12, 1681
32. Y.-C. Chen, H.- L. Cui, Organocatalytic Cascade Reactions, in: Science of Synthesis - Asymmetric Organocatalysis, Vol. 2, (Eds.: B. List, K. Maruoka), Thieme, Stuttgart, 2012, p 787
33. D. Bonne, T. Constantieux, Y. Coquerel, J. Rodriguez, Org. Biomol. Chem. 2012, 10, 3969
34. H. Pellissier, Adv. Synth. Catal. 2012, 354, 237
35. A. Grossmann, D. Enders, Angew. Chem. 2012, 124, 320
36. Angew. Chem. Int. Ed. 2012, 51, 314
37. B. Westermann, M. Ayaz, S. S. van Berkel, Angew. Chem. 2010, 122, 858
38. Angew. Chem. Int. Ed. 2010, 49, 846
39. C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167
40. X. Yu, W. Wang, Org. Biomol. Chem., 2008, 6, 2037
41. D. Enders, C. Grondal, M. R. M. Huettl, Angew. Chem. 2007, 119, 1590
42. Angew. Chem. Int. Ed. 2007, 46, 1570
43. G. Guillena, D. J. Ramon, M. Yus, Tetrahedron: Asymmetry 2007, 18, 693.
44. C. Enkisch, C. Schneider, Eur. J. Org. Chem. 2009, 5549
45. W. Zhang, J. Franzen, Adv. Synth. Catal. 2010, 352, 499
46. A. B. Northrup, D. W. C. MacMillan, Science 2004, 305, 1752.
47. X. Dou, Y. Lu, Chem. Eur. J. 2012, 18, 8315
48. J. Gao, S. Bai, Q. Gao, Y. Liu, Q. Yang, Chem. Commun. 2011, 47, 6716
49. X. Tian, C. Cassani, Y. Liu, A. Moran, A. Urakawa, P. Galzerano, E. Arceo, P. Melchiorre, J. Am. Chem. Soc. 2011, 133, 17934
50. M. Bandini, P. G. Cozzi, A. Umani-Ronchi, Angew. Chem. 2000, 112, 2417
51. Angew. Chem. Int. Ed. 2000, 39, 2327.
52. J. Marjanovic, V. Divjakovic, R. Matovic, Z. Ferjancic, R. N. Saicic, Eur. J. Org. Chem. 2013, 5555
53. J. D. Huber, J. L. Leighton, J. Am. Chem. Soc. 2007, 129, 14552.
54. M. T. Oliveira, M. Luparia, D. Audisio, N. Maulide, Angew. Chem. Int. Ed. 2013, 52, 13149
55. D. Audisio, M. Luparia, M. T. Oliveira, D. Klutt, N. Maulide, Angew. Chem. 2012, 124, 7426
56. Angew. Chem. Int. Ed. 2012, 51, 7314
57. G. Lu, T. Yoshino, H. Morimoto, S. Matsunaga, M. Shibasaki, Angew. Chem. 2011, 123, 4474
58. Angew. Chem. Int. Ed. 2011, 50, 4382
59. M. Luparia, M. T. Oliveira, D. Audisio, F. Frebault, R. Goddard, N. Maulide, Angew. Chem. 2011, 123, 12840
60. Angew. Chem. Int. Ed. 2011, 50, 12631
61. A. Nojiri, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 3779
62. X.-X. Yan, Q. Peng, Q. Li, K. Zhang, J. SounYao, X.-L. Hou, Y.-D. Wu, J. Am. Chem. Soc. 2008, 130, 14362
63. B. Wang, F. Wu, Y. Wang, X. Liu, L. Deng, J. Am. Chem. Soc. 2007, 129, 768.
64. N. K. Rana, H. Huang, J. C.-G. Zhao, Angew. Chem. 2014, 126, 7749
65. Angew. Chem. Int. Ed. 2014, 53, 7619
66. S. Krautwald, D. Sarlah, M. Schafroth, E. M. Carreira, Science 2013, 340, 1065
67. B. Simmons, A. M. Walji, D. W. C. MacMillan, Angew. Chem. 2009, 121, 4413
68. Angew. Chem. Int. Ed. 2009, 48, 4349
69. Y. Chi, S. T. Scroggins, J. M. J. Frechet, J. Am. Chem. Soc. 2008, 130, 6322.
70. S. Reboredo, E. Reyes, J. L. Vicario, D. Badia, L. Carrillo, A. de Cozar, F. P. Cossio, Chem. Eur. J. 2012, 18, 7179
71. G. Talavera, E. Reyes, J. L. Vicario, L. Carrillo, Angew. Chem. 2012, 124, 4180
72. Angew. Chem. Int. Ed. 2012, 51, 4104
73. E. Reyes, G. Talavera, J. L. Vicario, D. Badia, L. Carrillo, Angew. Chem. 2009, 121, 5811
74. Angew. Chem. Int. Ed. 2009, 48, 5701
75. J. L. Vicario, S. Reboredo, D. Badia, L. Carrillo, Angew. Chem. 2007, 119, 5260
76. Angew. Chem. Int. Ed. 2007, 46, 5168.
77. B. Tan, P. J. Chua, Y. Li, G. Zhong, Org. Lett. 2008, 10, 2437.
78. K. A. Jørgensen, An Organocatalytic Approach to Optically Active Six-Membered Rings, in: Asymmetric Synthesis - The Essentials, 2nd edn., (Eds.: M. Christmann, S. Brase), Wiley-VCH, Weinheim, 2008, p 200
79. S. Goudedranche, W. Raimondi, X. Bugaut, T. Constantieux, D. Bonne, J. Rodriguez, Synthesis 2013, 1909
80. T. Gasperi, P. Punzi, A. Migliorini, D. Tofani, Curr. Org. Chem. 2011, 15, 2098
81. P. Merino, E. Marques- Lopez, T. Tejero, R. P. Herrera, Synthesis 2010, 1909.
82. O. V. Serdyuk, Org. Biomol. Chem. 2013, 11, 7051
83. S. Narayanaperumal, Chem- CatChem 2013, 5, 2756
84. Y. Takemoto, Bifunctional Thiourea Catalysts, in: Asymmetric Synthesis II, (Eds.: M. Christmann, S. Brase), Wiley-VCH, Weinheim, 2012, p 233
85. L.-Q. Lu, Synlett 2012, 490
86. S. J. Connon, Chem. Commun. 2008, 2499
87. T. Marcelli, Angew. Chem. 2006, 118, 7658
88. Angew. Chem. Int. Ed. 2006, 45, 7496
89. S. J. Connon, Chem. Eur. J. 2006, 12, 5419.
90. B.-C. Hong, D.-J. Lan, N. S. Dange, G.-H. Lee, J.-H. Liao, Eur. J. Org. Chem. 2013, 2472
91. Z. Mao, Y. Jia, Z. Xu, R. Wang, Adv. Synth. Catal. 2012, 354, 1401
92. C. T. Wong, Tetrahedron 2012, 68, 481
93. D. Enders, R. Kruell, W. Bettray, Synthesis 2010, 567
94. Y. Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. 2007, 119, 5010
95. Angew. Chem. Int. Ed. 2007, 46, 4922.
96. J. L. Garcia-Ruano, V. Marcos, J. A. Suanzes, L. Marzo, J. Aleman, Chem. Eur. J. 2009, 15, 6576
97. E. Reyes, A. Jiang, A. Milleli, P. Elsner, R. T. Hazell, K. A. Jørgensen, Angew. Chem. 2007, 119, 9362
98. Angew. Chem. Int. Ed. 2007, 46, 9202.
99. D. Shi, Y. Xie, H. Zhou, C. Xia, H. Huang, Angew. Chem. 2012, 124, 1274
100. Angew. Chem. Int. Ed. 2012, 51, 1248
101. W. Li, X. Liu, Z. Mao, Q. Chen, R. Wang, Org. Biomol. Chem. 2012, 10, 4767.
102. R. Hahn, G. Raabe, D. Enders, Org. Lett. 2014, 16, 3636
103. P. Chauhan, S. Mahajan, C. C. J. Loh, G. Raabe, D. Enders, Org. Lett. 2014, 16, 2954
104. C. C. J. Loh, D. Hack, D. Enders, Chem. Commun. 2013, 49, 10230
105. D. Enders, R. Hahn, I. Atodiresei, Adv. Synth. Catal. 2013, 355, 1126
106. K. Albertshofer, B. Tan, C. F. Barbas III, Org. Lett. 2012, 14, 1834
107. S. Varga, G. Jakab, L. Drahos, T. Holczbauer, M. Czugler, T. Soos, Org. Lett. 2011, 13, 5416
108. M. Rueping, A. Kuenkel, R. Frchlich, Chem. Eur. J. 2010, 16, 4173
109. D. Ding, C.-G. Zhao, Q. Guo, H. Arman, Tetrahedron 2010, 66, 4423
110. B. Tan, Y. Lu, X. Zeng, P. J. Chua, G. Zhong, Org. Lett. 2010, 12, 2682.
111. L. S. Aitken, N. R. Arezki, A. Dell'Isola, A. J. A. Cobb, Synthesis 2013, 2627.
112. J. P. Malerich, K. Hagihara, V. H. Rawal, J. Am. Chem. Soc. 2008, 130, 14416.
113. J. Aleman, A. Parra, H. Jiang, K. A. Jørgensen, Chem. Eur. J. 2011, 17, 6890
114. Y. E. Turkmen, Y. Zhu, V. H. Rawal, Brønsted Acids, in: Comprehensive Enantioselective Organocatalysis, Vol. 2, (Ed.: P. I. Dalko), Wiley-VCH, Weinheim, 2013, chap. 10.
115. CCDC 995481 (3a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
116. CCDC 995483 (4a) contains the supplementary crystallographic data for this paper. These data can be ob- tained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
117. L. Albrecht, H. Jiang, K. A. Jørgensen, Angew. Chem. 2011, 123, 8642
118. Angew. Chem. Int. Ed. 2011, 50, 8492.
119. CCDC 995485 (11) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
120. CCDC 995486 (14a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
121. P. H.-Y. Cheong, C. Y. Legault, J. M. Um, N. Celebi-Olcum, K. N. Houk, Chem. Rev. 2011, 111, 5042.
122. B. Kotai, G. Kardos, A. Hamza, V. Farkas, I. Papai, T. Soos, Chem. Eur. J. 2014, 20, 5631.
123. A. Hamza, G. Schubert, T. Soos, I. Papai, J. Am. Chem. Soc. 2006, 128, 13151
124. T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119.