A versatile and highly stereoselective access to vinyl triflates derived from 1,3-dicarbonyl and related compounds

Journal of Organic Chemistry

Volumn 73, Issue 19, 2008, Pages 7845-7848

  Specklin, Simon ^a   Bertus, Philippe ^a,b   Weibel, Jean Marc ^a   Pale, Patrick ^a  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

^b UNIVERSITÉ DU MAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARSENIC COMPOUNDS; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; DICHLOROMETHANE; ESTERS; KETONES; LITHIUM; STEREOSELECTIVITY; SUGAR (SUCROSE);

CHEMICAL EQUATIONS; DIKETONES; ENOLIZATION; HIGH SELECTIVITY; KETOAMIDES; KETOESTERS; LITHIUM TRIFLATE; RELATED COMPOUNDS; STEREO-SELECTIVE; TRIFLATES;

ORGANIC COMPOUNDS;

CARBONYL DERIVATIVE; LITHIUM; TRIFLUOROMETHANESULFONIC ACID; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 53049084106     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8015049     Document Type: Article

References (39)

1. Ritter, K. Synthesis 1993, 735-762.
2. (a) Hargrove, R. J.; Stang, P. J. J. Org. Chem. 1974, 39, 581-582.
3. (b) Schwede, W.; Cleve, A.; Ottow, E.; Wiechert, R. Tetrahedron Lett. 1993, 34, 5257-5260.
4. (c) Stang, P. J.; Mangum, M. G.; Fox, D. P.; Haak, P. J. Am. Chem. Soc. 1974, 96, 4562-4569.
5. (d) Stang, P. J.; Fox, D. P.; Collins, C. J.; Watson, J. J. Org. Chem. 1978, 43, 364-365.
6. (e) Fleming, I.; Mwaniki, J. M. J. Chem. Soc., Perkin Trans. 1 1998, 1237-1248.
7. (a) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316, For synthetic applications, see i. a.
8. (b) Kant, J., Jr.; Baker, S. R. Tetrahedron Lett. 1990, 31, 3389-3392.
9. (c) Pearson, W. H.; Lee, III Y.; Mi, Y.; Stoy, P J. Org. Chem. 2004, 69, 9109-9122.
10. (a) Halbes-Letinois, U.; P. Pale, P. Palladium catalyzed synthesis of Enynes in Leading Edge Organometallic Chemistry Research : Cato, M. A., Ed.; Nova Publishers: New York, 2006, pp 93-131.
11. (b) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 2004.
12. (c) Negishi, E-i.; De Meijere, A. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley: New York, 2002.
13. Comins, D.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299-6302.
14. Wright, M. E.; Pulley, S. R. J. Org. Chem. 1989, 54, 2886-2889.
15. (a) Stang, P. J.; Treptow, W Synthesis 1980, 283-284.
16. (b) Crich, D.; Smith, M.; Q. Yao; Picione, J Synthesis 2001, 323-326.
17. (c) Herrera-fernandez, A.; Martinez-Alvarez, R.; Chioua, M.; Chioua, R.; Almy, J.; Loaiza, O. A. ARKIVOC 2007, xvi, 58-64.
18. See, i.a.: Keck, D.; Muller, T.; Bräse, S Synlett 2006, 3457-3460.
19. Vasilyev, A. V.; Walspurger, S.; Chassaing, S.; Pale, P.; Sommer, J. Eur. J. Org. Chem. 2007, 5740-5748.
20. (a) Hansen, A. L.; Skrydstrup, T. J. Org. Chem. 2005, 70, 5997-6003.
21. (b) Baxter, J. M.; Steinhuebel, D.; Palucki, M.; Davies, I. W. Org. Lett. 2005, 7, 215-218.
22. (c) Scheiper, B.; Bonnekessel, M.; Krause, H.; Fürstner, A. J. Org. Chem. 2004, 69, 3943-3949.
23. (d) Bio, M. M.; Leighton, J. L. Org. Lett. 2000, 2, 2905-2907.
24. (e) Romero, D. L.; Manninen, P. R.; Han, F.; Romero, A. G. J. Org. Chem. 1999, 64, 4980-4984.
25. (f) Kim, H.-O.; Ogbu, C. O.; Nelson, S.; Kahn, M. Synlett 1998, 1059-1060.
26. (g) Loreto, M. A. Tetrahedron 1997, 53, 15853-15858.
27. (h) Crisp, G. T.; Meyer, A. G. J. Org. Chem. 1992, 57, 6972-6975.
28. (i) Nakatani, K.; Arai, K.; Yamada, Y.; Terashima, S. Tetrahedron 1992, 48, 3045-3060.
29. (j) Brückner, R.; Scheuplien, S. W.; Suffert, J. Tetrahedron lett. 1991, 32, 1449-1452.
30. (k) Saulnier, M. G.; Kadow, J. F.; Tun, M. M.; Langley, D. R.; Vyas, D. M. J. Am. Chem. Soc. 1989, 111, 8320-8321.
31. (a) Evans, D. A.; Vogel, E.; Nelson, J. V J. Am. Chem. Soc. 1979, 101, 6120-6121.
32. (b) Evans, D.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099-3111.
33. (c) Von Horn, D. E.; Masamune, S. Tetrahedron Lett. 1979, 24, 2229-2232.
34. (d) Hirama, M.; Masamune, S. Tetrahedron Lett. 1979, 24, 2225-2228.
35. 3 did not give satisfactory results; 2 equiv of LiOTf was required to achieve high selectivity.
36. Brückner, S.; Abraham, E.; Klotz, P.; Suffert, J. Org. Lett. 2002, 4, 3391-3393.
37. (a) Nakatsuji, H.; Ueno, K.; Misaki, T; Tanabe, Y Org. Lett. 2008, 10, 2131-2134.
38. (b) Baxter, J. M.; Steinhuebel, D.; Palucki, M.; Davies, I. W. Org. Lett. 2005, 7, 215-218.
39. Simple amines only returned the starting materials.