Facile regio- and stereoselective metal-free synthesis of all-carbon tetrasubstituted alkenes bearing a C(sp3)-F unit via dehydroxyfluorination of morita-baylis-hillman (MBH) adducts

Organic Letters

Volumn 16, Issue 16, 2014, Pages 4162-4165

  Takizawa, Shinobu ^a   Arteaga, Fernando Arteaga ^a   Kishi, Kenta ^a   Hirata, Shuichi ^a   Sasai, Hiroaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84906220145     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501855m     Document Type: Article

References (84)

1. Wang, J., Ed. Stereoselective Alkene Synthesis in Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 2012.
2. Oger, C.; Balas, L.; Durand, T.; Galano, J.-M. Chem. Rev. 2012, 113, 1313
3. Nakao, Y. Bull. Chem. Soc. Jpn. 2012, 85, 731
4. Michaelides, I. N.; Dixon, D. J. Angew. Chem., Int. Ed. 2013, 52, 806
5. Greenhalgh, M. D.; Thomas, S. P. Synlett 2013, 24, 531
6. Kawaguchi, S.; Ogawa, A. Synlett 2013, 24, 2199
7. Deraedt, C.; d'Halluin, M.; Astruc, D. Eur. J. Inorg. Chem. 2013, 4881
8. Zhao, C.; Crimmin, M. R.; Toste, F. D.; Bergman, R. G. Acc. Chem. Res. 2014, 47, 517
9. Liu, X.; Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2004, 43, 879
10. Vicario, J.; Walko, M.; Meetsma, A.; Feringa, B. L. J. Am. Chem. Soc. 2006, 128, 5127
11. Nishihara, Y.; Miyasaka, M.; Okamoto, M.; Takahashi, H.; Inoue, E.; Tanemura, K.; Takagi, K. J. Am. Chem. Soc. 2007, 129, 12634
12. Arthuis, M.; Pontikis, R.; Florent, J.-C. J. Org. Chem. 2009, 74, 2234
13. He, Z.; Kirchberg, S.; Fröhlich, R.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 3699
14. Matsumoto, K.; Shindo, M. Adv. Synth. Catal. 2012, 354, 642
15. Liu, Y.; Lv, Y.; Xi, H.; Zhang, X.; Chen, S.; Lam, J. W. Y.; Kwok, R. T. K.; Mahtab, F.; Kwok, H. S.; Tao, X.; Tang, B. Z. Chem. Commun. 2013, 49, 7216
16. Nandakumar, A.; Perumal, P. T. Org. Lett. 2013, 15, 382
17. Flynn, A. B.; Ogilvie, W. W. Chem. Rev. 2007, 107, 4698
18. Mori, M. Eur. J. Org. Chem. 2007, 4981
19. Wang, Y.; Fordyce, E. A. F.; Chen, F. Y.; Lam, H. W. Angew. Chem., Int. Ed. 2008, 47, 7350
20. Shindo, M.; Mori, S. Synlett 2008, 2231
21. Negishi, E.; Huang, Z.; Wang, G.; Mohan, S.; Wang, C.; Hattori, H. Acc. Chem. Res. 2008, 41, 1474
22. Arai, T.; Ikematsu, Y.; Suemitsu, Y. Pure. Appl. Chem. 2010, 82, 1485
23. Stenne, B.; Timperio, J.; Savoie, J.; Dudding, T.; Collins, S. K. Org. Lett. 2010, 12, 2032
24. Ueda, M.; Matsubara, H.; Yoshida, K.; Sato, A.; Naito, T.; Miyata, O. Chem. - Eur. J. 2011, 17, 1789
25. Alfaro, R.; Parra, A.; Alemán, J.; Ruano, J. L. G.; Tortosa, M. J. Am. Chem. Soc. 2012, 134, 15165
26. You, W.; Li, Y.; Brown, M. K. Org. Lett. 2013, 15, 1610
27. Barczak, N. T.; Rooke, D. A.; Menard, Z. A.; Ferreira, E. M. Angew. Chem., Int. Ed. 2013, 52, 7579
28. Suero, M. G.; Bayle, E. D.; Collins, B. S. L.; Gaunt, M. J. J. Am. Chem. Soc. 2013, 135, 5332
29. Cao, C.-R.; Ou, S.; Jiang, M.; Liu, J.-T. Org. Biomol. Chem. 2014, 12, 467
30. Vercruysse, S.; Cornelissen, L.; Nahra, F.; Collard, L.; Riant, O. Chem. - Eur. J. 2014, 20, 1834
31. Aikawa, K.; Shimizu, N.; Honda, K.; Hioki, Y.; Mikami, K. Chem. Sci. 2014, 5, 410 and references therein
32. Landelle, G.; Bergeron, M.; Turcotte-Savard, M.-O.; Paquin, J.-F. Chem. Soc. Rev. 2011, 40, 2867
33. Berger, R.; Resnati, G.; Metrangolo, P.; Weber, E.; Hulliger, J. Chem. Soc. Rev. 2011, 40, 3496
34. Boldon, S.; Stenhagen, I. S. R.; Moore, J. E.; Luthra, S. K.; Gouverneur, V. Synthesis 2011, 24, 3929
35. Qiu, X.-L.; Qing, F.-L. Eur. J. Org. Chem. 2011, 3261
36. Yanai, H.; Taguchi, T. Eur. J. Org. Chem. 2011, 5939
37. Grygorenko, O. O.; Artamonov, O. S.; Komarov, I. V.; Mykhailiuk, P. K. Tetrahedron 2011, 67, 803
38. Laube, M.; Kniess, T.; Pietzsch, J. Molecules 2013, 18, 6311
39. Zhang, C.-P.; Chen, Q.-Y.; Guo, Y.; Xiao, J.-C.; Gu, Y.-C. Chem. Soc. Rev. 2012, 41, 4536
40. Giornal, F.; Pazenok, S.; Rodefeld, L.; Lui, N.; Vors, J.-P.; Leroux, F. R. J. Fluorine Chem. 2013, 152, 2
41. Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214
42. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432
43. Pacheco, M. C.; Purser, S.; Gouverneur, V. Chem. Rev. 2008, 108, 1943
44. Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2008, 47, 4157
45. Boldon, S.; Moore, J. E.; Gouverneur, V. Chem. Commun. 2008, 3622
46. Jiang, H.; Falcicchio, A.; Jensen, K. L.; Paixão, M. W.; Bertelsen, S.; Jørgensen, K. A. J. Am. Chem. Soc. 2009, 131, 7153
47. Katcher, M. H.; Doyle, A. G. J. Am. Chem. Soc. 2010, 132, 17402
48. Hollingworth, C.; Hazari, A.; Hopkinson, M. N.; Tredwell, M.; Benedetto, E.; Huiban, M.; Gee, A. D.; Brown, J. M.; Gouverneur, V. Angew. Chem., Int. Ed. 2011, 50, 2613
49. Katcher, M. H.; Sha, A.; Doyle, A. G. J. Am. Chem. Soc. 2011, 133, 15902
50. Topczewski, J. J.; Tewson, T. J.; Nguyen, H. M. J. Am. Chem. Soc. 2011, 133, 19318
51. Kiss, L.; Forró, E.; Fustero, S.; Fülöp, F. Org. Biomol. Chem. 2011, 9, 6528
52. Hollingworth, C.; Gouverneur, V. Chem. Commun. 2012, 48, 2929
53. Lauer, A. M.; Wu, J. Org. Lett. 2012, 14, 5138
54. Bloom, S.; Pitts, C. R.; Miller, D. C.; Haselton, N.; Holl, M. G.; Urheim, E.; Lectka, T. Angew. Chem., Int. Ed. 2012, 51, 10580
55. Wu, J.; Wang, Y.-M.; Drljevic, A.; Rauniyar, V.; Phipps, R. J.; Toste, F. D. Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 13729
56. Benedetto, E.; Tredwell, M.; Hollingworth, C.; Khotavivattana, T.; Brown, J. M.; Gouverneur, V. Chem. Sci. 2013, 4, 89
57. Braun, M.-G.; Doyle, A. G. J. Am. Chem. Soc. 2013, 135, 12990
58. Zhang, Z.; Wang, F.; Mu, X.; Chen, P.; Liu, G. Angew. Chem., Int. Ed. 2013, 52, 7549
59. Qin, C.; Davies, H. M. L. Org. Lett. 2013, 15, 6152
60. Larsson, J. M.; Pathipati, S. R.; Szabó, K. J. J. Org. Chem. 2013, 78, 7330
61. Katcher, M. H.; Norrby, P.-O.; Doyle, A. G. Organometallics 2014, 33, 2121
62. Shiuey, S.-J.; Kulesha, I.; Baggiolini, E. G.; Uskoković, M. R. J. Org. Chem. 1990, 55, 243
63. Boukerb, A.; Grée, D.; Laabassi, M.; Grée, R. J. Fluorine Chem. 1998, 88, 23 and references therein
64. Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447
65. Lima-Junior, C. G.; Vasconcellos, M. L. A. A. Bioorg. Med. Chem. 2012, 20, 3954
66. Wei, Y.; Shi, M. Chem. Rev. 2013, 113, 6659
67. Basavaiah, D.; Bharathi, T. K.; Gowriswari, V. V. L Tetrahedron Lett. 1987, 28, 4351
68. Basavaiah, D.; Muthukumaran, K.; Sreenivasulu, B. Synlett 1999, 1249
69. Basavaiah, D.; Sreenivasulu, B.; Reddy, R. M.; Muthukumaran, K. Synth. Commun. 2001, 31, 2987
70. Basavaiah, D.; Sreenivasulu, B.; Rao, A. J. J. Org. Chem. 2003, 68, 5983
71. Shi, M.; Zhang, W. Tetrahedron 2005, 61, 11887
72. Ma, D.; Yu, S.; Li, B.; Chen, L.; Chen, R.; Yu, K.; Zhang, L.; Chen, Z.; Zhong, D.; Gong, Z.; Wang, R.; Jiang, H.; Pei, G. ChemMedChem 2007, 2, 187
73. Basavaiah, D.; Devendar, B.; Aravindu, K.; Veerendhar, A. Chem. - Eur. J. 2010, 16, 2031
74. We found that a tetramethylguanidine and azole binary system also gave successful results for the MBH reaction of ketones. For aldehydes as starting materials, see: Terada, M.; Fukuchi, S.; Amagai, K.; Nakano, M.; Ube, H. ChemCatChem 2012, 4, 963
75. Scheeren, J. W.; Dahmen, F. J. M.; Bakker, C. G. Tetrahedron Lett. 1979, 20, 2925
76. Itoh, O.; Iwakoshi, N.; Saitoh, T.; Katano, H.; Fujisawa, Y.; Hasegawa, Y.; Sugita, T.; Ichikawa, K. Bull. Chem. Soc. Jpn. 1982, 55, 177
77. Santry, L. J.; McClelland, R. A. J. Am. Chem. Soc. 1983, 105, 6138
78. Gururaja, G. N.; Mobin, S. M.; Namboothiri, I. N. N. Eur. J. Org. Chem. 2011, 2048
79. Crystallographic data of E-2q for structural analysis have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 977587. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: (+44) 1223-336-033; E-mail: deposit@ccdc.cam.ac.uk or www: http://www.ccdc.cam.ac.uk/data-request/cif.
80. Singh, R. P.; Majumder, U.; Shreeve, J. M. J. Org. Chem. 2001, 66, 6263
81. Linderman, R. J. Oxetanes and Oxetenes Comprehensive Heterocyclic Chemistry II 1996, 1B, 721
82. Ruano, J. L. G.; Fernández-Ibáñez, M. A.; Fernández-Salas, J. A.; Maestro, M. C.; Márquez-López, P.; Rodríguez-Fernández, M. M. J. Org. Chem. 2009, 74, 1200
83. Takizawa, S.; Inoue, N.; Hirata, S.; Sasai, H. Angew. Chem., Int. Ed. 2010, 49, 9725
84. Foucaud, A.; Bakouetila, M. Synthesis 1987, 854