A Versatile Organocatalytic Approach for the Synthesis of Enantioenriched gem-Difluorinated Compounds

Chemistry - A European Journal

Volumn 21, Issue 39, 2015, Pages 13689-13695

  Saulnier, Steve ^a   Ciardi, Moira ^a,b   Lopez Carrillo, Veronica ^a   Gualandi, Andrea ^a   Cozzi, Pier Giorgio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

aldehydes; alkylation; enantioselectivity; fluorine; organocatalysis

Indexed keywords

ALDEHYDES; ALKYLATION; FLUORINATION; FLUORINE; HALOGENATION; SELECTIVE CATALYTIC REDUCTION; STEREOCHEMISTRY; STEREOSELECTIVITY;

BUILDING BLOCKES; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; ORGANOCATALYSIS; ORGANOCATALYTIC; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS; SYNTHETIC STRATEGIES;

ENANTIOSELECTIVITY;

EID: 84941599453     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201502099     Document Type: Article

References (102)

1. K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881;
2. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320;
3. W. K. Hagmann, J. Med. Chem. 2008, 51, 4359;
4. E. Leclerc, X. Pannecoucke, M. Ethève-Quelquejeuc, M. Sollogoub, Chem. Soc. Rev. 2013, 42, 4270; for a comprehensive review on fluorination, see:
5. T. Liang, C. N. Neumann, T. Ritter, Angew. Chem. Int. Ed. 2013, 52, 8214;
6. Angew. Chem. 2013, 125, 8372.
7. D. O'Hagan, Chem. Soc. Rev. 2008, 37, 308;
8. N. A. Meanwell, J. Med. Chem. 2011, 54, 2529;
9. M. A. Chowdhury, K. R. Abdellatif, Y. Dong, D. Das, M. R. Suresh, E. E. Knaus, J. Med. Chem. 2009, 52, 1525;
10. J. A. Erickson, J. I. McLoughlin, J. Org. Chem. 1995, 60, 1626;
11. R. Chen, D. G. Gorenstein, W. P. Kennedy, G. Lowe, D. Nurse, R. M. Schultz, Biochemistry 1979, 18, 921;
12. G. Lowe, D. Nurse, J. Chem. Soc. Chem. Commun. 1977, 815b.
13. X. Yang, T. Wu, R. J. Phipps, F. D. Toste, Chem. Rev. 2015, 115, 826;
14. M. G. Campbell, T. Ritter, Chem. Rev. 2015, 115, 612;
15. T. Ahrens, J. Kohlmann, M. Ahrens, T. Braun, Chem. Rev. 2015, 115, 931;
16. D. O'Hagan, H.-I. Deng, Chem. Rev. 2015, 115, 634.
17. J. Charpentier, N. Früh, A. Togni, Chem. Rev. 2015, 115, 650;
18. X. Liu, C. Xu, M. Wang, Q. Liu, Chem. Rev. 2015, 115, 683;
19. C. Alonso, E. M. deMarigorta, G. Rubiales, F. Palacios, Chem. Rev. 2015, 115, 1847;
20. O. A. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475.
21. Y. Guo, J. M. Shreeve, Chem. Commun. 2007, 3583;
22. K. Fujikawa, Y. Fujioka, A. Kobayashi, H. Amii, Org. Lett. 2011, 13, 5560;
23. P. S. Fier, J. F. Hartwig, J. Am. Chem. Soc. 2012, 134, 5524;
24. G. K. S. Prakash, S. K. Ganesh, J.-P. Jones, A. Kulkarni, K. Masood, J. K. Swabeck, G. A. Olah, Angew. Chem. Int. Ed. 2012, 51, 12090;
25. Angew. Chem. 2012, 124, 12256;
26. K. Araki, M. Inoue, Tetrahedron 2013, 69, 3913;
27. Q. Qi, Q. Shen, L. Lu, J. Am. Chem. Soc. 2012, 134, 6548;
28. Q.-Q. Min, Z. Yin, Z. Feng, W.-H. Guo, X. Zhang, J. Am. Chem. Soc. 2014, 136, 1230;
29. S. Ge, W. Chaładaj, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 4149;
30. Z. Feng, Q.-Q. Min, Y.-L. Xiao, B. Zhang, X. Zhang, Angew. Chem. Int. Ed. 2014, 53, 1669;
31. Angew. Chem. 2014, 126, 1695;
32. Y.-L. Xiao, W.-H. Guo, G.-Z. He, Q. Pan, X. Zhang, Angew. Chem. Int. Ed. 2014, 53, 9909;
33. Angew. Chem. 2014, 126, 10067;
34. Y.-B. Yu, G.-Z. He, X. Zhang, Angew. Chem. Int. Ed. 2014, 53, 10457;
35. Angew. Chem. 2014, 126, 10625;
36. S. Ge, S. I. Arlow, M. G. Mormino, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 14401;
37. C. Matheis, K. Jouvin, L. J. Goossen, Org. Lett. 2014, 16, 5984;
38. Y. Gu, X. Leng, Q. Shen, Nat. Commun. 2014, 5, 5405;
39. S.-L. Shi, S. L. Buchwald, Angew. Chem 2015, 127, 1666.
40. J. Wang, M. Sánchez-Rosellõ, J. L. Aceña, C. delPozo, A. E. Sorochinsky, S. Fustero, V. A. Soloshonok, H. Liu, Chem. Rev. 2014, 114, 2432;
41. J. F. Liebman, A. Greenberg, J. W. R. Dolbier, Fluorine-Containing Molecules: Structure, Reactivity, Synthesis and Applications, Wiley-VCH, Weinheim, 1988; for asymmetric difluorination, see:
42. K. Panigrahi, G. A. Applegate, G. Malik, D. B. Berkowitz, J. Am. Chem. Soc. 2015, 137, 3600;
43. W. Thaharn, D. Soorukram, C. Kuhakarn, P. Tuchinda, C. Pakawatchai, S. Saithong, V. Reutrakul, M. Pohmakotr, J. Org. Chem. 2015, 80, 816;
44. P. V. Ramachandran, A. Tafelska-Kaczmarek, A. Chatterjee, J. Org. Chem. 2012, 77, 9329;
45. W. Kashikura, K. Mori, T. Akiyama, Org. Lett. 2011, 13, 1860;
46. Y. Li, S. J. Miller, J. Org. Chem. 2011, 76, 9785; for a rare example of enantioselective difluorination, see:
47. O. Lozano, G. Blessley, T. MartinezdelCampo, A. L. Thompson, G. T. Giuffredi, M. Bettati, M. Walker, R. Borman, V. Gouverneur, Angew. Chem. Int. Ed. 2011, 50, 8105;
48. Angew. Chem. 2011, 123, 8255.
49. S. N. Crane, W. C. Black, J. T. Palmer, D. E. Davis, E. Setti, J. Robichaud, J. Paquet, R. M. Oballa, C. I. Bayly, D. J. McKay, J. R. Somoza, N. Chauret, C. Seto, J. Scheigetz, G. Wesolowski, F. Massé, S. Desmarais, M. Ouellet, J. Med. Chem. 2006, 49, 1066; 2:
50. G. Hirai, T. Watanabe, K. Yamaguchi, T. Miyagi, M. Sodeoka, J. Am. Chem. Soc. 2007, 129, 15420; 3:
51. G. Gumina, R. F. Schinazi, C. K. Chu, Org. Lett. 2001, 3, 4177;
52. X. Zhang, H. Xia, X. Dong, J. Jin, W.-D. Meng, F.-L. Qing, J. Org. Chem. 2003, 68, 9026; 4:
53. G. Verniest, R. Surmont, E. V. Hende, A. Deweweire, F. Deroose, J. W. Thuring, N. DeKimpe, J. Org. Chem. 2008, 73, 5458; 5:
54. J. A. Codelli, J. M. Baskin, N. J. Agard, C. R. Bertozzi, J. Am. Chem. Soc. 2008, 130, 11486; 6:
55. X. Yue, X. Zhang, F.-L. Qing, Org. Lett. 2009, 11, 73; 7:
56. T. Itoh, K. Sakabe, K. Kudo, H. Ohara, Y. Takagi, H. Kihara, P. Zagatti, M. Renou, J. Org. Chem. 1999, 64, 252; 8:
57. M. I. Barrena, M. I. Matheu, S. Castillõn, J. Org. Chem. 1998, 63, 2184; 9:
58. J. Qiu, R. B. Silverman, J. Med. Chem. 2000, 43, 706;
59. S. Fustero, M. Sánchez-Rosellõ, J. L. Aceña, B. Fernández, A. Asensio, J. F. Sanz-Cervera, C. d. Pozo, J. Org. Chem. 2009, 74, 3414; 10 (Maraviroc):
60. D. A. Price, S. Gayton, M. D. Selby, J. Ahman, S. Haycock-Lewandowski, B. L. Stammen, A. Warren, Tetrahedron Lett. 2005, 46, 5005; 11 (Vinflunine):
61. E. Giovanelli, S. Leroux, L. Moisan, H. Carreyre, P. Thuéry, D.-A. Buisson, A. Meddour, J.-M. Coustard, S. Thibaudeau, B. Rousseau, M. Nicolas, P. Hellier, E. Doris, Org. Lett. 2011, 13, 4116;
62. J. Fahy, A. Duflos, J.-P. Ribet, J.-C. Jacquesy, C. Berrier, M.-P. Jouannetaud, F. Zunino, J. Am. Chem. Soc. 1997, 119, 8576.
63. G. A. Boswell, W. C. Rapika, R. M. Scriber, C. W. Tullock, Org. React. 1974, 21, 1.
64. M. G. Campbell, T. Ritter, Chem. Rec. 2014, 14, 482;
65. C. P. Zhang, Q. Y. Chen, Y. Guo, J. C. Xiao, Tetrahedron 2013, 69, 10955;
66. S. Rozen, Adv. Synth. Catal. 2010, 352, 2691.
67. G. C. Geary, E. G. Hope, K. Singh, A. M. Stuart, Chem. Commun. 2013, 49, 9263;
68. N. O. Ilchenko, B. O. A. Tasch, K. J. Szabõ, Angew. Chem. Int. Ed. 2014, 53, 12897;
69. Angew. Chem. 2014, 126, 13111.
70. F. Liu, A. Martin-Mingot, M.-P. Jouannetaud, C. Bachmann, G. Frapper, F. Zunino, S. Thibaudeau, J. Org. Chem. 2011, 76, 1460;
71. E. Vardelle, A. Martin-Mingot, M.-P. Jouannetaud, C. Bachmann, J. Marrot, S. Thibaudeau, J. Org. Chem. 2009, 74, 6025.
72. Q. Zhou, A. Ruffoni, R. Gianatassio, Y. Fujiwara, E. Sella, D. Shabat, P. S. Baran, Angew. Chem. Int. Ed. 2013, 52, 3949;
73. Angew. Chem. 2013, 125, 4041.
74. J. H. Jones, C. Appayee, S. E. Brenner-Moyer, Eur. J. Org. Chem. 2014, 5273. For a review of stereoselective organocatalytic fluorinations, see:
75. J.-H. Lin, J.-C. Xiao, Tetrahedron Lett. 2014, 55, 6147.
76. C. N. Neumann, T. Ritter, Angew. Chem. Int. Ed. 2015, 54, 3216;
77. Angew. Chem. 2015, 127, 3261.
78. J. Kollonitsch, S. Marburg, L. M. Perkins, J. Org. Chem. 1976, 41, 3107;
79. S. C. Sondej, J. A. Katzenellenbogen, J. Org. Chem. 1986, 51, 3508;
80. C. York, G. K. S. Prakash, G. A. Olah, Tetrahedron 1996, 52, 9;
81. K. C. Nicolaou, R. Dolle, D. Papahatjis, J. L. Randall, J. Am. Chem. Soc. 1984, 106, 4189.
82. A. Gualandi, E. Emer, M. G. Capdevila, P. G. Cozzi, Angew. Chem. Int. Ed. 2011, 50, 7842;
83. Angew. Chem. 2011, 123, 7988;
84. A. Gualandi, L. Mengozzi, P. G. Cozzi, Chem. Today 2014, 32, 14;
85. A. Gualandi, L. Mengozzi, J. Giacoboni, S. Saulnier, M. Ciardi, P. G. Cozzi, Chirality 2014, 26, 607;
86. A. Gualandi, P. Canestrari, E. Emer, P. G. Cozzi, Adv. Synth. Catal. 2014, 356, 528;
87. D. Petruzziello, A. Gualandi, H. Jaffar, V. Lopez-Carrillo, P. G. Cozzi, Eur. J. Org. Chem. 2013, 4909;
88. A. Gualandi, M. Emma, J. Giacoboni, L. Mengozzi, P. G. Cozzi, Synlett 2013, 449;
89. R. Porta, M. Benaglia, A. Puglisi, A. Mandoli, A. Gualandi, P. G. Cozzi, ChemSusChem 2014, 7, 3534.
90. S. Karlsson, H.-E. Hçgberg, Synthesis 2000, 1863.
91. M. S. Wiehn, S. D. Lindell, S. Bräse, Angew. Chem. Int. Ed. 2008, 47, 8120-8122;
92. Angew. Chem. 2008, 120, 8240-8242;; for a review, see:
93. M. Kuroboshi, K. Kanie, T. Hiyama, Adv. Synth. Catal. 2001, 343, 235.
94. In the reduction of the ketone moiety there is a slight preference for the cis-diastereoisomer (the relative configuration was determined by H-H coupling constant analysis)
95. One of the characterized by-products was 2-benzyloxy-cyclohexylbenzo[b]-1,4-dithiine, formed by a rearrangement of the 1,3-benzodithiol. See the Supporting Information for GC-MS.
96. In ref.[16a], acid-free 20 was used in the presence of NaH2PO4. The new protocol (see the Supporting Information) involves the use of commercially available 20 without any bases, slighting improving yields and ee values; see also ref.[16d].
97. A. Gualandi, D. Petruzziello, E. Emer, P. G. Cozzi, Chem. Commun. 2012, 48, 3614.
98. To obtain good yield in the alkylation of benzodithiol derivatives it is important to use good quality nBuLi and to add the correct amount. nBuLi must be titrated prior to use in this reaction (see the Supporting Information).
99. D. A. Nagib, M. E. Scott, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 10875.
100. R. A. Fernandes, A. B. Ingle, Curr. Med. Chem. 2013, 20, 2315;
101. B. Gaye, A. Adejare, Future Med. Chem. 2009, 1, 821
102. M. Yanagisawa, T. Aida, T. Takeda, K. Namekata, T. Harada, R. Shinagawa, K. Tanaka, Cell Death Dis. 2015, 6, e 1693.