Asymmetric decarboxylative 1,4-addition of malonic acid half thioesters to vinyl sulfones: Highly enantioselective synthesis of 3-monofluoromethyl-3- arylpropanoic esters

Chemistry - An Asian Journal

Volumn 9, Issue 5, 2014, Pages 1252-1256

  Qiao, Baokun ^a   Liu, Qian ^a   Liu, Hongjun ^a   Yan, Lin ^a   Jiang, Zhiyong ^a  

^a HENAN UNIVERSITY   (China)

Author keywords

asymmetric synthesis; decarboxylative 1,4 addition; monofluoromethylation; organocatalysis; vinyl sulfones

Indexed keywords

CARBOXYLIC ACIDS; REACTION KINETICS; THIOUREAS;

1 ,4-ADDITION; ASYMMETRIC SYNTHESIS; MONOFLUOROMETHYLATION; ORGANOCATALYSIS; VINYL SULFONES;

ENANTIOSELECTIVITY;

MALONIC ACID DERIVATIVE; PROPIONIC ACID DERIVATIVE; SULFONE;

CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

MALONATES; MOLECULAR STRUCTURE; PROPIONATES; STEREOISOMERISM; SULFONES;

EID: 84899423033     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201400049     Document Type: Article

References (93)

1. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Eds.:, R. Filler, Y. Kobayashi, L. M. Yagupolskii,), Elsevier, 1993
2. T. Hiyama, in Organofluorine Compounds: Chemistry and Applications, Springer, Berlin, 2000
3. K. Uneyama, in Organofluorine Chemistry, Blackwell, Oxford, 2006
4. D. OHagan, Chem. Soc. Rev. 2008, 37, 308
5. Y. Wang, Y.-C. Luo, X.-Q. Hu, P.-F. Xu, Org. Lett. 2011, 13, 5346
6. T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470.
7. For selected reviews, see
8. J.-A. Ma, D. Cahard, Chem. Rev. 2004, 104, 6119
9. H. Ibrahim, A. Togni, Chem. Commun. 2004, 1147
10. P. M. Pihko, Angew. Chem. Int. Ed. 2006, 45, 544
11. Angew. Chem. 2006, 118, 558
12. V. A. Brunet, D. O'Hagan, Angew. Chem. Int. Ed. 2008, 47, 1179
13. Angew. Chem. 2008, 120, 1198
14. S. Lectard, Y. Hamashima, M. Sodeoka, Adv. Synth. Catal. 2010, 352, 2708
15. D. Cahard, X. Xu, S. Couve-Bonnaire, X. Pannecoucke, Chem. Soc. Rev. 2010, 39, 558
16. C. Hollingworth, V. Gouverneur, Chem. Commun. 2012, 48, 2929.
17. V. K. Honwad, A. S. Rao, Tetrahedron 1965, 21, 2593
18. A. I. Meyers, D. Stoianova, J. Org. Chem. 1997, 62, 5219
19. C. Fuganti, S. Serra, A. Dulio, J. Chem. Soc. Perkin Trans. 1 1999, 279
20. C. Fuganti, S. Serra, J. Chem. Soc. Perkin Trans. 1 2000, 3758
21. M. Osaka, M. Kanematsu, M. Yoshida, K. Shishido, Tetrahedron: Asymmetry 2010, 21, 2319.
22. A. Abate, E. Brenna, C. D. Negri, C. Fuganti, S. Serra, Tetrahedron: Asymmetry 2002, 13, 899
23. P. Kraft, J. Chem. Educ. 2010, 87, 598.
24. J. Almy, D. J. Cram, J. Am. Chem. Soc. 1969, 91, 4459
25. W. M. Welch, A. R. Kraska, R. Sarges, B. K. Koe, J. Med. Chem. 1984, 27, 1508
26. J. A. Lowe, D. L. Hageman, S. E. Drozda, S. McLean, D. K. Bryce, R. T. Crawford, S. Zorn, J. Morrone, J. Bordner, J. Med. Chem. 1994, 37, 3789
27. J. Yun, S. L. Buchwald, J. Org. Chem. 2000, 65, 767
28. F. O. Arp, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 10482.
29. P. Ghorai, A. Kraus, T. Birnkammer, R. Geyer, G. Bernhardt, S. Dove, R. Seifert, S. Elz, A. Buschauer, Bioorg. Med. Chem. Lett. 2010, 20, 3173.
30. Y. Pan, Y. Zhao, T. Ma, Y. Yang, H. Liu, Z. Jiang, C.-H. Tan, Chem. Eur. J. 2010, 16, 779
31. Y. Zhao, Y. Pan, H. Liu, Y. Yang, Z. Jiang, C.-H. Tan, Chem. Eur. J. 2011, 17, 3571
32. W. Yang, X. Wei, Y. Pan, R. Lee, B. Zhu, H. Liu, L. Yan, K.-W. Huang, Z. Jiang, C.-H. Tan, Chem. Eur. J. 2011, 17, 8066
33. L. Yan, Z. Han, B. Zhu, C. Yang, C.-H. Tan, Z. Jiang, Beilstein J. Org. Chem. 2013, 9, 1853.
34. D. Liu, W. Tang, X. Zhang, Org. Lett. 2004, 6, 513
35. D. liu, Q. Dai, X. Zhang, Tetrahedron 2005, 61, 6460
36. C.-J. Hou, W.-L. Guo, X.-P. Hu, J. Deng, Z. Zheng, Tetrahedron: Asymmetry 2011, 22, 195
37. J. Mazuela, P.-O. Norrby, P. G. Andersson, O. Pàmies, M. Diéguez, J. Am. Chem. Soc. 2011, 133, 13634
38. J.-Q. Li, X. Quan, P. G. Andersson, Chem. Eur. J. 2012, 18, 10609.
39. S. Oi, A. Taira, Y. Honma, Y. Inoue, Org. Lett. 2003, 5, 97
40. S. Oi, A. Taira, Y. Honma, T. Sato, Y. Inoue, Tetrahedron: Asymmetry 2006, 17, 598
41. R. Shintani, T. Kimura, T. Hayashi, Chem. Commun. 2005, 3213
42. L. Navarre, M. Pucheault, S. Darses, J.-P. Genet, Tetrahedron Lett. 2005, 46, 4247
43. S.-Y. Wang, T.-P. Loh, Chem. Commun. 2010, 46, 8694
44. L. Gremaud, A. Alexakis, Angew. Chem. Int. Ed. 2012, 51, 794
45. Angew. Chem. 2012, 124, 818.
46. A.-N. Alba, X. Companyõ, A. Moyano, R. Rios, Chem. Eur. J. 2009, 15, 7035
47. S. Zhang, Y. Zhang, Y. Ji, H. Li, W. Wang, Chem. Commun. 2009, 4886
48. F. Ullah, G.-L. Zhao, L. Deiana, M. Zhu, P. Dziedzic, I. Ibrahem, P. Hammar, J. Sun, A. Cõrdova, Chem. Eur. J. 2009, 15, 10013.
49. For selected reviews, see
50. A. Hill, Nat. Prod. Rep. 2006, 23, 256
51. Y. Pan, C.-H. Tan, Synthesis 2011, 2044; For selected asymmetric decarboxylative reactions, see
52. S. Orlandi, M. Benaglia, F. Cozzi, Tetrahedron Lett. 2004, 45, 1747
53. D. Magdziak, G. Lalic, H. M. Lee, K. C. Fortner, A. D. Aloise, M. D. Shair, J. Am. Chem. Soc. 2005, 127, 7284
54. F. Berrué, S. Antoniotti, O. P. Thomas, P. Amade, Eur. J. Org. Chem. 2007, 1743
55. A. Ricci, D. Pettersen, L. Bernardi, F. Fini, M. Fochi, R. P. Herrera, V. Sgarzani, Adv. Synth. Catal. 2007, 349, 1037
56. J. Lubkoll, H. Wennemers, Angew. Chem. Int. Ed. 2007, 46, 6841
57. Angew. Chem. 2007, 119, 6965
58. M. Furutachi, S. Mouri, S. Matsunaga, M. Shibasaki, Chem. Asian J. 2010, 5, 2351
59. H. Y. Bae, S. Some, J. H. Lee, J.-Y. Kim, M. J. Song, S. Lee, Y. J. Zhang, C. E. Song, Adv. Synth. Catal. 2011, 353, 3196
60. N. Hara, S. Nakamura, Y. Funahashi, N. Shibata, Adv. Synth. Catal. 2011, 353, 2976
61. N. Hara, S. Nakamura, M. Sano, R. Tamura, Y. Funahashi, N. Shibata, Chem. Eur. J. 2012, 18, 9276
62. Y. Pan, C. W. Kee, Z. Jiang, T. Ma, Y. Zhao, Y. Yang, H. Xue, C.-H. Tan, Chem. Eur. J. 2011, 17, 8363
63. H. Y. Bae, H. J. Sim, J.-W. Lee, B. List, C. E. Song, Angew. Chem. Int. Ed. 2013, 52, 12143
64. Angew. Chem. 2013, 125, 12365.
65. For the examples through the formation of a covalent intermediate of the catalyst and the substrate, see
66. Q. Zhu, Y. Lu, Org. Lett. 2008, 10, 4803
67. A. Landa, M. Maestro, C. Masdeu, Á. Puente, S. Vera, M. Oiarbide, C. Palomo, Chem. Eur. J. 2009, 15, 1562; the first example of hydrogen-bond catalysis with 2-aryl-substituted vinyl sulfones as electrophiles was reported by Lu group
68. X. Dou, Y. Lu, Org. Biomol. Chem. 2013, 11, 5217.
69. For selected reviews, see
70. P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289
71. T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999
72. M. S. Taylor, E. N. Jacobsen, Angew. Chem. Int. Ed. 2006, 45, 1520
73. Angew. Chem. 2006, 118, 1550
74. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713
75. S. J. Connon, Chem. Commun. 2008, 2499
76. X. Yu, W. Wang, Chem. Asian J. 2008, 3, 516.
77. X. Li, H. Deng, B. Zhang, J. Li, L. Zhang, S. Luo, J.-P. Cheng, Chem. Eur. J. 2010, 16, 450
78. X. Li, B. Zhang, Z.-G. Xi, S. Luo, J.-P. Cheng, Adv. Synth. Catal. 2010, 352, 416
79. P. Li, G. Zhao, S. Zhu, Chin. J. Chem. 2011, 29, 2749.
80. J. P. Malerich, K. Hagihara, V. H. Rawal, J. Am. Chem. Soc. 2008, 130, 14416
81. W.-H. Wang, T. Abe, X.-B. Wang, K. Kodama, T. Hirose, G.-Y. Zhang, Tetrahedron: Asymmetry 2010, 21, 2925
82. H.-P. Deng, Y. Wei, M. Shi, Eur. J. Org. Chem. 2011, 1956
83. H. J. Lee, S. H. Kang, D. Y. Kim, Synlett 2011, 1559.
84. CCDC 980639 (3m) 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.
85. Q. Zhu, Y. Lu, Angew. Chem. Int. Ed. 2010, 49, 7753
86. Angew. Chem. 2010, 122, 7919.
87. W. Zhang, D. Tan, R. Lee, G. Tong, W. Chen, B. Qi, K.-W. Huang, C.-H. Tan, Z. Jiang, Angew. Chem. 2012, 124, 10216
88. Angew. Chem. Int. Ed. 2012, 51, 10069
89. B. Zhu, W. Zhang, R. Lee, Z. Han, W. Yang, D. Tan, K.-W. Huang, Z. Jiang, Angew. Chem. Int. Ed. 2013, 52, 6666
90. Angew. Chem. 2013, 125, 6798.
91. K. Kundu, J. V. McCullagh, A. T. Morehead, Jr., J. Am. Chem. Soc. 2005, 127, 16042
92. Y. Oonishi, J. Ogura, Y. Sato, Tetrahedron Lett. 2007, 48, 7505
93. M. M. Knudsen, N. Kalashnyk, F. Masini, J. R. Cramer, E. Lægsgaard, F. Besenbacher, T. R. Linderoth, K. V. Gothelf, J. Am. Chem. Soc. 2011, 133, 4896.