Synthesis of gem -difluoromethylenated compounds employing α,α-difluoro-α-phenylsulfanyl-α-trimethylsilylmethane (PhSCF2SiMe3) as a gem -difluoromethylene building block

Synlett

Volumn 25, Issue 18, 2014, Pages 2558-2573

  Soorukram, Darunee ^a   Kuhakarn, Chutima ^a   Reutrakul, Vichai ^a   Pohmakotr, Manat ^a  

^a Mahidol University   (Thailand)

Author keywords

fluorine; indolizidines; pyrrolizidines; radical cyclization; succinic anhydrides; succinimides; sulfur

Indexed keywords

1,1 DIFLUOROALKENE; ALKENE DERIVATIVE; ALPHA, ALPHA DIFLUORO ALPHA PHENYLSULFANYL ALPHA TRIMETHYLSILYLMETHANE; CARBONYL DERIVATIVE; CYCLOOCTANE DERIVATIVE; CYCLOPENTANOL DERIVATIVE; ESTER DERIVATIVE; FLUORIDE; FLUORINE DERIVATIVE; INDOLIZIDINE DERIVATIVE; KETONE DERIVATIVE; LACTONE DERIVATIVE; PENTANOL; PHTHALIMIDE DERIVATIVE; PYRROLIZIDINE DERIVATIVE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DIFLUOROMETHYLENATION; FLUORINATION; METHYLATION; NUCLEOPHILICITY; SYNTHESIS;

EID: 84911869938     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0034-1379164     Document Type: Article

References (110)

1. Enantiocontrolled Challenges and Biochemical Targets. Soloshonok V. A. John Wiley & Sons Chichester: 1999
2. Selective Fluorination in Organic and Bioorganic Chemistry. Welch J. T. American Chemical Society Washington, DC: 1990
3. Welch J. T. Tetrahedron: 1987; 43 3123
4. Resnati G. Tetrahedron: 1993; 49 9385
5. Kitazume T., Yamazaki T. Top. Curr. Chem.: 1997; 193 91
6. Percy J. M. Top. Curr. Chem.: 1997; 193 131
7. O'Hagan D., Rzepa H. S. Chem. Commun.: 1997; 645
8. Schlosser M. Angew. Chem. Int. Ed.: 1998; 37 1496
9. Sutherland A., Willis C. L. Nat. Prod. Rep.: 2000; 17 621
10. Smart B. E. J. Fluorine Chem.: 2001; 109 3
11. Organofluorine Compounds, Chemistry and Applications. Hiyama T. Springer New York: 2000
12. Hiyama T., Shimizu M. Angew. Chem. Int. Ed.: 2005; 44 214
13. Zemtsov A. A., Kondratyev N. S., Levin V. V., Struchkova M. I., Dilman A. D. J. Org. Chem.: 2014; 79 818
14. Salomon P., Zard S. Z. Org. Lett.: 2014; 16 1482
15. Min Q.-Q, Yin Z., Feng Z., Guo W.-H, Zhang X. J. Am. Chem. Soc.: 2014; 136 1230
16. Ni C., Hu J. Synthesis: 2014; 46 842
17. Munemori D., Narita K., Nokami T., Itoh T. Org. Lett.: 2014; 16 2638
18. Hashimoto R., Iida T., Aikawa K., Ito S., Mikami K. Chem. Eur. J.: 2014; 20 2750
19. Prakash G. K. S, Krishnamoorthy S., Ganesh S. K., Kulkarni A., Haiges R., Olah G. A. Org. Lett.: 2014; 16 54
20. Feng Z., Min Q.-Q, Xiao Y.-L, Zhang B., Zhang X. Angew. Chem. Int. Ed.: 2014; 53 1669
21. Lee G. M., Harrison D. J., Korobkov I., Baker R. T. Chem. Commun.: 2014; 50 1128
22. Wang J.-Y, Su Y.-M, Yin F., Bao Y., Zhang X., Xu Y.-M, Wang X.-S. Chem. Commun.: 2014; 50 4108
23. Li W., Zhu X., Mao H., Tang Z., Cheng Y., Zhu C. Chem. Commun.: 2014; 50 7521
24. Ma G., Wan W., Hu Q., Jiang H., Wang J., Zhu S., Hao J. Chem. Commun.: 2014; 50 7527
25. Hu M., He Z., Gao B., Li L., Ni C., Hu J. J. Am. Chem. Soc.: 2013; 135 17302
26. Prakash G. K. S, Ni C., Wang F., Zhang Z., Haiges R., Olah G. A. Angew. Chem. Int. Ed.: 2013; 52 10835
27. Mehta V. P., Greaney M. F. Org. Lett.: 2013; 15 5036
28. Zhou Q., Ruffoni A., Gianatassio R., Fujiwara Y., Sella E., Shabat D., Barran P. S. Angew. Chem. Int. Ed.: 2013; 52 3949
29. Chia P. W., Bello D., Slawin A. M. Z, O'Hagan D. Chem. Commun.: 2013; 49 2189
30. Li L., Wang F., Ni C., Hu J. Angew. Chem. Int. Ed.: 2013; 52 12390
31. Mykhailiuk P. K., Starova V., Iurchenko V., Shishkina S. V., Shishkin O. V., Khilchevskyi O., Zaporozhets O. Tetrahedron: 2013; 69 4066
32. Thomoson C. S., Dolbier W. R. Jr. J. Org. Chem.: 2013; 78 8904
33. Sakamoto T., Horiguchi K., Saito K., Mori K., Akiyama T. Asian J. Org. Chem.: 2013; 2 943
34. Orbegozo T., Burel F., Jubault P., Pannecoucke X. Tetrahedron: 2013; 69 4015
35. Zhao Y., Huang W., Zheng J., Hu J. Org. Lett.: 2011; 13 5342
36. Fourrière G., Hijfte N. V., Lalot J., Dutech G., Fragnet B., Coadou G., Quirion J.-C, Leclerc E. Tetrahedron: 2010; 66 3963
37. Yue X., Zhang X., Qing F.-L. Org. Lett.: 2009; 11 73
38. Diab S. A., Sene A., Pfund E., Lequeux T. Org. Lett.: 2008; 10 3895
39. Xu W., Dolbier W. R. Jr, Salazar J. J. Org. Chem.: 2008; 73 3535
40. Jakowiecki J., Loska R., Makosza M. J. Org. Chem.: 2008; 73 5436
41. Hang X.-C, Chen Q.-Y, Xiao J.-C. Synlett: 2008; 1989
42. Huguenot F., Billac A., Brigand T., Portella C. J. Org. Chem.: 2008; 73 2564
43. Beier P., Alexandrova A. V., Zibinsky M., Prakash G. K. S. Tetrahedron: 2008; 64 10977
44. Ramachandran V. P., Chatterjee A. Org. Lett.: 2008; 10 1195
45. Uneyama K. J. Fluorine Chem.: 2008; 129 550
46. Verniest G., Surmont R., Hende E. V., Deweweire A., Deroose F., Thuring J. W., De Kimpe N. J. Org. Chem.: 2008; 73 5458
47. Guo Y., Fujiwara K., Amii H., Uneyama K. J. Org. Chem.: 2007; 72 8523
48. Arimitsu S., Hammond G. B. J. Org. Chem.: 2007; 72 8559
49. Fustero S., Fernández B., Sanz-Cervera J. F., Mateu N., Mosulén S., Carbajo R. J., Pineda-Lucena A., Ramírez de Arellano C. J. Org. Chem.: 2007; 72 8716
50. You Z.-W, Jiang Z.-X, Wang B.-L, Qing F.-L. J. Org. Chem.: 2006; 71 7261
51. Fustero S., Sánchez-Roselló M., Rodrigo V., del Pozo C., Sanz-Cervera J. F., Simón A. Org. Lett.: 2006; 8 4129
52. Arimitsu S., Hammond G. B. J. Org. Chem.: 2006; 71 8665
53. Zheng F., Zhang X.-H, Qiu X.-L, Zhang X., Qing F.-L. Org. Lett.: 2006; 8 6083
54. Wang R.-W, Qing F.-L. Org. Lett.: 2005; 7 2189
55. Crowley P. J., Fawcett J., Griffith G. A., Moralee A. C., Percy J. M., Salafia V. Org. Biomol. Chem.: 2005; 3 3297
56. De Kimpe N., Van Brabandt W. Synlett: 2006; 2039
57. Qin Y.-Y, Yang Y.-Y, Qiu X.-L, Qing F.-L. Synthesis: 2006; 1475
58. Sato K., Tarui A., Matsuda S., Omote M., Ando A., Kumadaki I. Tetrahedron Lett.: 2005; 46 7679
59. Niida A., Mizumoto M., Narumi T., Inokuchi E., Oishi S., Ohno H., Otaka A., Kitaura K., Fujii N. J. Org. Chem.: 2006; 71 4118
60. You Z.-W, Zhang X., Qing F.-L. Synthesis: 2006; 2535
61. Betterley N. M., Surawatanawong P., Prabpai S., Kongsaeree P., Kuhakarn C., Pohmakotr M., Reutrakul V. Org. Lett.: 2013; 15 5666; and references cited therein
62. Belhomme M.-C, Poisson T., Pannecoucke X. Org. Lett.: 2013; 15 3428
63. Caillot G., Dufour J., Belhomme M.-C, Poisson T., Grimaud L., Pannecoucke X., Gillaizeau I. Chem. Commun.: 2014; 50 5887
64. Belhomme M.-C, Poisson T., Pannecoucke X. J. Org. Chem.: 2014; 79 7205
65. Poisson T., Belhomme M.-C, Pannecoucke X. J. Org. Chem.: 2012; 77 9277
66. Surapanich N., Kuhakarn C., Pohmakotr M., Reutrakul V. Eur. J. Org. Chem.: 2012; 5943
67. Qin Y.-Y, Qiu X.-L, Yang Y.-Y, Meng W.-D, Qing F.-L. J. Org. Chem.: 2005; 70 9040
68. Fourrière G., Lalot J., Van Hijfte N., Quirion J.-C, Leclerc E. Tetrahedron Lett.: 2009; 50 7048
69. Fourrière G., Van Hijfte N., Lalot J., Dutech G., Fragnet B., Coadou G., Quirion J.-C, Leclerc E. Tetrahedron: 2010; 66 3963
70. Suda M., Hino C. Tetrahedron Lett.: 1981; 22 1997
71. Burton D. J., Wiemers D. M. J. Fluorine Chem.: 1981; 18 573
72. Rico I., Wakselman C. Tetrahedron Lett.: 1981; 22 323
73. Rico I., Wakselman C. Tetrahedron: 1981; 37 4209
74. Prakash G. K. S, Hu J., Wang Y., Olah G. A. J. Fluorine Chem.: 2005; 126 529
75. Mizuta S., Shibata N., Ogawa S., Fujimoto H., Nakamura S., Toru T. Chem. Commun.: 2006; 2575
76. Li Y., Hu J. Angew. Chem. Int. Ed.: 2007; 46 2489
77. Prakash G. K. S, Hu J. Acc. Chem. Res.: 2007; 40 921
78. Li Y., Hu J. J. Fluorine Chem.: 2008; 129 382
79. Ferry A., Billard T., Langlois B. R., Bacque E. J. Org. Chem.: 2008; 73 9362
80. Paillard E., Toulgoat F., Arvai R., Iojoiu C., Cointeaux L., Medebielle M., Alloin F., Langlois B., Sanchez J.-Y. J. Fluorine Chem.: 2011; 132 1213
81. Kosobokov M. D., Dilman A. D., Struchkova M. I., Belyakov P. A., Hu J. J. Org. Chem.: 2012; 77 2080
82. Huang W., Hi C., Zhao Y., Zhang W., Dilman A. D., Hu J. Tetrahedron: 2012; 68 5137
83. Levin V. V., Elkin P. K., Struchkova M. I., Dilman A. D. J. Fluorine Chem.: 2013; 154 43
84. Ma J.-A, Cahard D. Chem. Rev.: 2004; 104 6119
85. Dilman A. D., Levin V. V. Eur. J. Org. Chem.: 2011; 831
86. Gawronski J., Wascinska N., Gajewy J. Chem. Rev.: 2008; 108 5227
87. Liu M., Li J., Xiao X., Xie Y., Shi Y. Chem. Commun.: 2013; 49 1404
88. Hoffman-Röder A., Seiler P., Diederich F. Org. Biomol. Chem.: 2004; 2 2267
89. Mizuta S., Shibata N., Sato T., Fujimoto H., Nakamura S., Toru T. Synlett: 2006; 267
90. Kawai H., Tachi K., Tokunaga E., Shiro M., Shibata N. Org. Lett.: 2010; 12 5104
91. Wu Y., Deng L. J. Am. Chem. Soc.: 2012; 134 14334
92. Masusai C., Soorukram D., Kuhakarn C., Tuchinda P., Reutrakul V., Pohmakotr M. J. Fluorine Chem.: 2013; 154 37
93. Masusai C., Soorukram D., Kuhakarn C., Tuchinda P., Pakawatchai C., Saithong S., Reutrakul V., Pohmakotr M. Org. Biomol. Chem.: 2013; 11 6650
94. Noyori R., Yokoyama K., Sakata J., Kuwajima I., Nakamura E., Shimizu M. J. Am. Chem. Soc.: 1977; 99 1265
95. Hosomi A., Araki Y., Sakurai H. J. Org. Chem.: 1983; 48 3122
96. Takano S., Numata H., Ogasawara K. Heterocycles: 1983; 20 417
97. Majetich G., Desmond R., Casares A. M. Tetrahedron Lett.: 1983; 24 1913
98. Dondoni A., Fantin G., Fogagnolo M., Medici A. Angew. Chem., Int. Ed. Engl.: 1986; 25 835
99. Mukaiyama T., Fujisawa H., Nakagawa T. Helv. Chim. Acta: 2002; 85 4518
100. Michida M., Toriumi T., Mukaiyama T. Tetrahedron Lett.: 2009; 50 3261
101. Beckwith A. L. J, Zimmermann J. J. Org. Chem.: 1991; 56 5791
102. Beckwith A. L. J, Schiesser C. H. Tetrahedron: 1985; 41 3925
103. Spellmeyer D. C., Houk K. N. J. Org. Chem.: 1987; 52 959
104. Bootwicha, T.; Panichakul, D.; Kuhakarn, C.; Prabpai, S.; Kongsaeree, P.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M. J. Org. Chem. 2009, 74, 3798.
105. Thaharn, W.; Bootwicha, T.; Soorukram, D.; Kuhakarn, C.; Prabpai, S.; Kongsaeree, P.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M. J. Org. Chem. 2012, 77, 8465.
106. Pharikronburee, V.; Punirun, T.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M. Org. Biomol. Chem. 2013, 11, 2022.
107. Pohmakotr, M.; Panichakul, D.; Tuchinda, P.; Reutrakul, V. Tetrahedron 2007, 63, 9429.
108. Chatupheeraphat, A.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pakawatchai, C.; Saithong, S.; Pohmakotr, P. Eur. J. Org. Chem. 2013, 6844.
109. Punirun, T.; Peewasan, K.; Kuhakarn, C.; Soorukram, D.; Tuchinda, P.; Reutrakul, V.; Kongsaeree, P.; Prabpai, S.; Pohmakotr, M. Org. Lett. 2012, 14, 1820.
110. Thaharn, W.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M. Angew. Chem. Int. Ed. 2014, 53, 2212.