Rhodium-catalyzed asymmetric cycloisomerization of 1,6-ene-ynamides

Advanced Synthesis and Catalysis

Volumn 355, Issue 7, 2013, Pages 1374-1382

  Nishimura, Takahiro ^a   Takiguchi, Yuka ^a   Maeda, Yuko ^a   Hayashi, Tamio ^b,c  

^a KYOTO UNIVERSITY   (Japan)

^b INSTITUTE OF MATERIALS RESEARCH AND ENGINEERING   (Singapore)

^c NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

asymmetric synthesis; chiral diene; cycloisomerization; ene ynamides; rhodium

Indexed keywords

EID: 84877695480     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300148     Document Type: Article

References (99)

1. B. M. Trost, Acc. Chem. Res. 1990, 23, 34
2. B. M. Trost, A. S. K. Hashmi, Angew. Chem. 1993, 105, 1130
3. Angew. Chem. Int. Ed. Engl. 1993, 32, 1085
4. B. M. Trost, A. S. K. Hashmi, J. Am. Chem. Soc. 1994, 116, 2183
5. B. M. Trost, A. S. K. Hashmi, R. G. Ball, Adv. Synth. Catal. 2001, 343, 490.
6. G. C. Lloyd-Jones, Org. Biomol. Chem. 2003, 1, 215
7. A. M. Echavarren, C. Nevado, Chem. Soc. Rev. 2004, 33, 431
8. C. Bruneau, Angew. Chem. 2005, 117, 2380
9. Angew. Chem. Int. Ed. 2005, 44, 2328
10. L. Zhang, J. Sun, S. A. Kozmin, Adv. Synth. Catal. 2006, 348, 2271
11. A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478
12. Angew. Chem. Int. Ed. 2007, 46, 3410
13. V. Michelet, P. Y. Toullec, J.-P. Genêt, Angew. Chem. 2008, 120, 4338
14. Angew. Chem. Int. Ed. 2008, 47, 4268
15. E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326
16. H. C. Shen, Tetrahedron 2008, 64, 7847
17. S. I. Lee, N. Chatani, Chem. Commun. 2009, 371.
18. A. Pradal, P. Y. Toullec, V. Michelet, Synthesis 2011, 1501
19. I. D. G. Watson, F. D. Toste, Chem. Sci. 2012, 3, 2899
20. A. Marinetti, H. Jullien, A, Voituriez, Chem. Soc. Rev. 2012, 41, 4884.
21. J. Blum, H. Beer-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567
22. A. Fürstner, H. Szillat, F. Stelzer, J. Am. Chem. Soc. 2000, 122, 6785
23. M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511
24. A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863
25. C. Nevado, C. Ferrer, A. M. Echavarren, Org. Lett. 2004, 6, 3191
26. A. Fürstner, P. W. Davies, T. Gress, J. Am. Chem. Soc. 2005, 127, 8244
27. E. J. Cho, M. Kim, D. Lee, Org. Lett. 2006, 8, 5413
28. A. Hercouet, F. Berrée, C. H. Lin, L. Toupet, B. Carboni, Org. Lett. 2007, 9, 1717
29. C. Ferrer, M. Raducan, C. Nevado, C. K. Claverie, A. M. Echavarren, Tetrahedron 2007, 63, 6306
30. D. Olagnier, P. Costes, A. Berry, M.-D. Linas, M. Urrutigoity, O. Dechy-Cabaret, F. Benoit-Vical, Bioorg. Med. Chem. Lett. 2007, 17, 6075
31. J.-B. Xia, W.-B. Liu, T.-M. Wang, S.-L. You, Chem. Eur. J. 2010, 16, 6442
32. L. Elitzin, B. Liu, M. Sharp, E. Tabet, Tetrahedron Lett. 2011, 52, 3518.
33. C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456
34. Angew. Chem. Int. Ed. 2004, 43, 2402
35. S. I. Lee, S. M. Kim, S. Y. Kim, Y. K. Chung, Synlett 2006, 2256
36. S. Lee, S. M. Kim, M. R. Choi, S. Kim, Y. K. Chung, J. Org. Chem. 2006, 71, 9366
37. S. M. Kim, J. H. Park, S. Y. Choi, Y. K. Chung, Angew. Chem. 2007, 119, 6284
38. Angew. Chem. Int. Ed. 2007, 46, 6172
39. Z. Chen, Y.-X. Zhang, Y.-H. Wang, L.-L. Zhu, H. Liu, X.-X. Li, L. Guo, Org. Lett. 2010, 12, 3468.
40. P. Costes, J. Weckesser, O. Dechy-Cabaret, M. Urrutigoïty, P. Kalck, Appl. Organomet. Chem. 2008, 22, 211.
41. S. H. Sim, S. I. Lee, J. H. Park, Y. K. Chung, Adv. Synth. Catal. 2010, 352, 317
42. E. Benedetti, A. Simonneau, A. Hours, H. Amouri, A. Penoni, G. Palmisano, M. Malacria, J.-P. Goddard, L. Fensterbank, Adv. Synth. Catal. 2011, 353, 1908.
43. C. Fehr, I. Farris, H. Sommer, Org. Lett. 2006, 8, 1839
44. C. Fehr, M. Vuagnoux, H. Sommer, Chem. Eur. J. 2011, 17, 3832.
45. F. Micheli, P. Cavanni, D. Andreotti, R. Arban, R. Benedetti, B. Bertani, M. Bettati, L. Bettelini, G. Bonanomi, S. Braggio, R. Carletti, A. Checchia, M. Corsi, E. Fazzolari, S. Fontana, C. Marchioro, E. Merlo-Pich, M. Negri, B. Oliosi, E. Ratti, K. D. Read, M. Roscic, I. Sartori, S. Spada, G. Tedesco, L. Tarsi, S. Terreni, F. Visentini, A. Zocchi, L. Zonzini, R. Di Fabio, J. Med. Chem. 2010, 53, 4989.
46. T. Shibata, Y. Kobayashi, S. Maekawa, N. Toshida, K. Takagi, Tetrahedron 2005, 61, 9018.
47. M. Barbazanges, M. Augé, J. Moussa, H. Amouri, C. Aubert, C. Desmarets, L. Fensterbank, V. Gandon, M. Malacria, C. Ollivier, Chem. Eur. J. 2011, 17, 13789.
48. D. Brissy, M. Skander, P. Retailleau, A. Marinetti, Organometallics 2007, 26, 5782
49. D. Brissy, M. Skander, P. Retailleau, G. Frison, A. Marinetti, Organometallics 2009, 28, 140
50. D. Brissy, M. Skander, H. Jullien, P. Retailleau, A. Marinetti, Org. Lett. 2009, 11, 2137
51. H. Jullien, D. Brissy, R. Sylvain, P. Retailleau, J.-V. Naubron, S. Gladiali, A. Marinetti, Adv. Synth. Catal. 2011, 353, 1109.
52. C.-M. Chao, D. Beltrami, P. Y. Toullec, V. Michelet, Chem. Commun. 2009, 6988
53. A. Pradal, C.-M. Chao, P. Y. Toullec, V. Michelet, Beilstein J. Org. Chem. 2011, 7, 1021.
54. N. M. Deschamps, V. I. Elitzin, B. Liu, M. B. Mitchell, M. J. Sharp, E. A. Tabet, J. Org. Chem. 2011, 76, 712.
55. H. Teller, A. Fürstner, Chem. Eur. J. 2011, 17, 7764
56. H. Teller, M. Corbet, L. Mantilli, G. Gopakumar, R. Goddard, W. Thiel, A. Fürstner, J. Am. Chem. Soc. 2012, 134, 15331.
57. H. Jullien, D. Brissy, P. Retailleau, A. Marinetti, Eur. J. Inorg. Chem. 2011, 5083
58. A. Martínez, P. García-García, M. A. Fernández-Rodriíguez, F. Rodríguez, R. Sanz, Angew. Chem. 2010, 122, 4737
59. Angew. Chem. Int. Ed. 2010, 49, 4633.
60. T. Nishimura, T. Kawamoto, M. Nagaosa, H. Kumamoto, T. Hayashi, Angew. Chem. 2010, 122, 1682
61. Angew. Chem. Int. Ed. 2010, 49, 1638
62. T. Nishimura, Y. Maeda, T. Hayashi, Org. Lett. 2011, 13, 3674.
63. J. A. Feducia, A. N. Campbell, M. Q. Doherty, M. R. Gagné, J. Am. Chem. Soc. 2006, 128, 13290.
64. Y. Shibata, K. Noguchi, K. Tanaka, J. Am. Chem. Soc. 2010, 132, 7896.
65. F. Marion, J. Coulomb, C. Courillon, L. Fensterbank, M. Malacria, Org. Lett. 2004, 6, 1509
66. S. Couty, C. Meyer, J. Cossy, Angew. Chem. 2006, 118, 6878
67. Angew. Chem. Int. Ed. 2006, 45, 6726. For examples of gold-catalyzed furan-yne cycloisomerization, see
68. A. S. K. Hashmi, M. Rudolph, J. W. Bats, W. Frey, F. Rominger, T. Oeser, Chem. Eur. J. 2008, 14, 6672
69. A. S. K. Hashmi, S. Pankajakshan, M. Rudolph, E. Enns, T. Bander, F. Rominger, W. Frey, Adv. Synth. Catal. 2009, 351, 2855.
70. C. Defieber, H. Grützmacher, E. M. Carreira, Angew. Chem. 2008, 120, 4558
71. Angew. Chem. Int. Ed. 2008, 47, 4482
72. R. Shintani, T. Hayashi, Aldrichimica Acta 2009, 42, 31
73. C. G. Feng, M.-H. Xu, G.-Q. Lin, Synlett 2011, 1345. For selected examples of chiral diene ligands, see
74. T. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida, J. Am. Chem. Soc. 2003, 125, 11508
75. Y. Otomaru, K. Okamoto, R. Shintani, T. Hayashi, J. Org. Chem. 2005, 70, 2503
76. K. Okamoto, T. Hayashi, V. H. Rawal, Chem. Commun. 2009, 4815
77. C. Fischer, C. Defieber, T. Suzuki, E. M. Carreira, J. Am. Chem. Soc. 2004, 126, 1628
78. J.-F. Paquin, C. Defieber, C. R. J. Stephenson, E. M. Carreira, J. Am. Chem. Soc. 2005, 127, 10850
79. F. Läng, F. Breher, D. Stein, H. Grützmacher, Organometallics 2005, 24, 2997
80. S. Helbig, S. Sauer, N. Cramer, S. Laschat, A. Baro, W. Frey, Adv. Synth. Catal. 2007, 349, 2331
81. Z.-Q. Wang, C.-G. Feng, M.-H. Xu, G.-Q. Lin, J. Am. Chem. Soc. 2007, 129, 5336
82. T. Noël, K. Vandyck, J. Van der Eycken, Tetrahedron 2007, 63, 12961
83. T. Gendrineau, O. Chuzel, H. Eijsberg, J.-P. Genet, S. Darses, Angew. Chem. 2008, 120, 7783
84. Angew. Chem. Int. Ed. 2008, 47, 7669
85. X. Hu, M. Zhuang, Z. Cao, H. Du, Org. Lett. 2009, 11, 4744
86. M. K. Brown, E. J. Corey, Org. Lett. 2010, 12, 172
87. Y. Luo, A. J. Carnell, Angew. Chem. 2010, 122, 2810
88. Angew. Chem. Int. Ed. 2010, 49, 2750
89. G. Pattison, G. Piraux, H. W. Lam, J. Am. Chem. Soc. 2010, 132, 14373.
90. T. Nishimura, H. Kumamoto, M. Nagaosa, T. Hayashi, Chem. Commun. 2009, 5713.
91. T. Nishimura, J. Wang, M. Nagaosa, K. Okamoto, R. Shintani, F. Kwong, W. Yu, A. S. C. Chan, T. Hayashi, J. Am. Chem. Soc. 2010, 132, 464
92. T. Nishimura, Y. Takiguchi, T. Hayashi, J. Am. Chem. Soc. 2012, 134, 9086.
93. The absolute structure was deduced based on the Flack parameter [0.08(5)]. CCDC 918290 (compound 2a) 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.
94. C. Nevado, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2003, 9, 2627
95. E. Soriano, P. Ballesteros, J. Marco-Contelles, J. Org. Chem. 2004, 69, 8018
96. E. Soriano, J. Marco-Contelles, Acc. Chem. Res. 2009, 42, 1026.
97. T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052.
98. N. Dieltiens, K. Moonen, C. V. Stevens, Chem. Eur. J. 2007, 13, 203.
99. T. Hamada, X. Ye, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 833.