Stereoselective synthesis of both stereoisomers of β-fluorostyrene derivatives from a common intermediate

Organic Letters

Volumn 13, Issue 6, 2011, Pages 1568-1571

  Landelle, Grégory ^a   Turcotte Savard, Marc Olivier ^a   Angers, Laetitia ^a   Paquin, Jean François ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINATED HYDROCARBON; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; STEREOISOMERISM; STYRENES;

EID: 79952577870     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200302h     Document Type: Article

References (54)

1. For selected book/reviews/accounts, see: Hiyama, T. In Organofluorine Compounds; Chemistry and Applications; Yamamoto, H., Ed.; Springer: 2000, and references therein.
2. Smart, B. E. J. Fluorine Chem. 2001, 109, 3-11
3. Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 106, 6119-6146
4. Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214-231
5. Thayer, A. M. Chem. Eng. News 2006, 84, 15-24
6. Kirk, K. L. J. Fluorine Chem. 2006, 127, 1013-1029
7. Bégué, J.-P.; Bonnet-Delpon, D. J. Fluorine Chem. 2006, 127, 992-1012
8. Prakash, G. K. S.; Hu, J. Acc. Chem. Res. 2007, 40, 921-930
9. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886
10. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330
11. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359-4369
12. Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1-PR43
13. For our own efforts in this area, see: Bélanger, É.; Cantin, K.; Messe, O.; Tremblay, M.; Paquin, J.-F. J. Am. Chem. Soc. 2007, 129, 1034-125
14. Bélanger, É.; Houzé, C.; Guimond, N.; Cantin, K.; Paquin, J.-F. Chem. Commun. 2008, 3251-3253
15. Landelle, G.; Champagne, P. A.; Barbeau, X.; Paquin, J.-F. Org. Lett. 2009, 11, 681-684
16. Landelle, G.; Turcotte-Savard, M.-O.; Marterer, J.; Champagne, P. A.; Paquin, J.-F. Org. Lett. 2009, 11, 5406-5409
17. Pigeon, X.; Bergeron, M.; Barabé, F.; Dubé, P.; Frost, H. N.; Paquin, J.-F. Angew. Chem., Int. Ed. 2010, 49, 1123-1127
18. For a review on the synthesis of terminal monofluoroalkenes including β-fluorostyrenes, see: van Steenis, J. H.; van der Gen, A. J. Chem. Soc., Perkin Trans. 1 2002, 2117-2133
19. Schlosser, M.; Zimmermann, M. Synthesis 1969, 75-76
20. Inbasekaran, M.; Peet, N. P.; McCarthy, J. R.; LeTourneau, M. E. J. Chem. Soc., Chem. Commun. 1985, 678-679
21. Petasis, N. A.; Yudin, A. K.; Zavialov, I. A.; Prakash, G. K. S.; Olah, G. A. Synlett 1997, 606-608
22. Wang, Q.; Wei, H.-x.; Schlosser, M. Eur. J. Org. Chem. 1999, 3263-3268
23. Zhu, L.; Ni, C.; Zhao, Y.; Hu, J. Tetrahedron 2010, 66, 5089-5100
24. Prakash, G. K. S; Shakhmin, A.; Zibinsky, M.; Ledneczki, I.; Chacko, S.; Olah, G. A. J. Fluorine Chem. 2010, 131, 1192-1197
25. Schlosser, M.; Christmann, K.-F. Synthesis 1969, 38-39
26. Burton, D. J.; Greenlimb, P. E. J. Org. Chem. 1975, 40, 2796-2801
27. Hayashi, S.-i.; Nakai, T.; Ishikawa, N.; Burton, D. J.; Naae, D. G.; Kesling, H. S. Chem. Lett. 1979, 983-986
28. Cox, D. G.; Gurusamy, N.; Burton, D. J. J. Am. Chem. Soc. 1985, 107, 2811-2812
29. Purrington, S. T.; Pittman, J. H. Tetrahedron Lett. 1987, 28, 3901-3904
30. Uno, H.; Sakamoto, K.; Semba, F.; Suzuki, H. Bull. Chem. Soc. Jpn. 1992, 65, 210-217
31. Galli, C.; Guarnieri, A.; Koch, H.; Mencarelli, P.; Rappoport, Z. J. Org. Chem. 1997, 62, 4072-4077
32. Kataoka, K.; Tsuboi, S. Synthesis 2000, 452-456
33. van Steenis, J. H.; van der Gen, A. Eur. J. Org. Chem. 2001, 897-910
34. Greedy, B.; Gouverneur, V. Chem. Commun. 2001, 233-234
35. Lee, S.-H.; Schwartz, J. J. Am. Chem. Soc. 1986, 108, 2445-2447
36. Lee, S.-H.; Riediker, M.; Schwartz, J. Bull. Korean Chem. Soc. 1998, 19, 760-766
37. Furuya, T.; Ritter, T. Org. Lett. 2009, 11, 2860-2863
38. 2N(F) t -Bu is not commercially available and has to be prepared using elemental fluorine.
39. Marterer, J.; Paquin, J.-F. Unpublished results.
40. Chan, T. H.; Fleming, I. Synthesis 1979, 761-786
41. Oda, H.; Sato, M.; Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron 1985, 41, 3257-3268
42. Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press Limited: London, 1988, and references therein.
43. See Supporting Information for more details.
44. Bach, R. D.; Evans, J. C. J. Am. Chem. Soc. 1986, 108, 1374-1379 and references therein
45. Cho, B. R.; Cho, N. S.; Lee, S. K. J. Org. Chem. 1997, 62, 2230-2233 and references therein
46. Xu, J.; Burton, D. J. Org. Lett. 2002, 4, 831-833
47. Goumans, T. P. M.; van Alem, K.; Lodder, G. Eur. J. Org. Chem. 2008, 435-443
48. Ernet, T.; Haufe, G. Tetrahedron Lett. 1996, 37, 7251-7252
49. Ernet, T.; Maulitz, A. H.; Würthwein, E.-U.; Haufe, G. J. Chem. Soc., Perkin Trans. 1 2001, 1929-1938
50. For other examples where the selectivity of a Diels-Alder reaction is influenced by the presence of a fluorine atom, see: Crowley, P. J.; Percy, J. M.; Stansfield, K. Tetrahedron Lett. 1996, 37, 8237-8240
51. Percy, J. M. Top. Curr. Chem. 1997, 193, 131-195
52. Ito, H.; Saito, A.; Taguchi, T. Tetrahedron Lett. 1998, 9, 1979-1987
53. Ito, H.; Saito, A.; Taguchi, T. Tetrahedron Lett. 1998, 9, 1988-1994
54. Haufe, G. In Vinyl Fluorides in Cycloadditions, in Fluorinated Synthons; Soloshonok, V., Ed.; ACS Symposium Series 911; American Chemical Society: Washington, D.C., 2005; pp 155 - 172.