Difluorinated Danishefsky's Diene: A versatile C4 building block for the fluorinated six-membered rings

Organic Letters

Volumn 3, Issue 20, 2001, Pages 3103-3105

  Amii, Hideki ^a   Kobayashi, Takeshi ^a   Terasawa, Hiroshi ^a   Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000103818     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0163631     Document Type: Article

References (35)

1. Oppolzer, W. Intermolecular Diels-Alder Reactions. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991, Vol. 5, pp 315-400.
2. (a) Petrzilka, M.; Grayson, J. I. Synthesis 1981, 753.
3. (b) Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction: Wiley: New York, 1990.
4. Reviews: (a) Danishefsky, S. Acc. Chem. Res. 1981, 14, 400.
5. (b) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15.
6. (c) Danishefsky, S. Chemtracts-Org. Chem. 1989, 2, 273.
7. Synthesis and application of difluorinated 1,3-dienes: (a) Shi, G. Q.; Schlosser, M. Tetrahedron 1993, 49, 1445.
8. (b) Jin, F.; Xu, Y.; Huang, W. J. Chem. Soc., Chem. Commun. 1993, 814.
9. (c) Jin, F.; Xu, Y.; Huang, W. J. Fluorine Chem. 1995, 71, 1.
10. (d) Shen. Q.; Hammond, G. B. Org. Lett. 2001, 3, 2213
11. Taguchi, T.; Kodama, Y.; Kanazawa, M. Carbohydr. Res. 1993, 249, 243.
12. Hojo, M.; Masuda, R.; Kokuryo, Y.; Shioda, H.; Matsuo, S. Chem. Lett. 1976, 499.
13. Colla, A.; Martins, M. A. P.; Clar, G.; Krimmer, S.; Fischer, P. Synthesis 1991, 483.
14. 19F NMR using 4, 4′-difluoro diphenylmethane as an internal standard.
15. (a) Chaussard, J.; Folest, J.-C.; Nedelec, J.-Y.; Périchon, J.; Sibille, S.; Troupel, M. Synthesis 1990, 369.
16. (b) Saboureau, C.; Troupel, M.; Sibille, S.; Périchon, J. J. Chem. Soc., Chem. Commun. 1989, 1138.
17. (c) Cavel, P.; Legar-lambert, M. P.; Biran, C.; Serein-Spirau, F.; Bordeau, M.; Roques, N.; Marzouk, H. Synthesis 1999, 829.
18. (d) Andrieux, C. P.; Combellas, C.; Kanoufi, F.; Savéant, J.-M.; Thiébault, A. J. Am. Chem. Soc. 1997, 119, 9527.
19. Electrochemical preparation of difluoromethyl compounds: (a) Uneyama, K.; Maeda, K.; Kato, T.; Katagiri, T. Tetrahedron Lett. 1998, 39, 3741.
20. (b) Uneyama, K.; Kato, T. Tetrahedron Lett. 1998, 39, 587.
21. (c) Uneyama, K.; Mizutani, G. Chem. Commun. 1999, 613.
22. (d) Uneyama, K.; Mizutani G.; Maeda, K.; Kato, T. J. Org. Chem. 1999, 64, 6717.
23. Mg(0)-promoted preparation of difluoro silyl enol ethers: (a) Amii, H.; Kobayashi, T.; Hatamoto, Y.; Uneyama, K. Chem. Commu. 1999, 1323.
24. (b) Amii, H.; Kobayashi, T.; Uneyama, K. Synthesis 2000, 2001.
25. (c) Mae, M.: Amii, H.; Uneyama, K. Tetrahedron Lett. 2000, 41, 7893.
26. Hetero Diels-Alder reaction of fluorinated aldimines: Crousse, B.; Begue, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009.
27. Preparation of iminoester 5d: Tietze, L. F.; Bratz, M. Synthesis 1989, 439.
28. Monteiro, H. J. The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1968; Vol. XI, p 145.
29. Hava, M., The Pharmacology of Vinca Species and their Alkaloids, The Vinca Alkaloids; Taylor, W. I., Farnsworth, N. R., Eds.; Marcel Dekker: New York, 1973; Chapter 6, p 305.
30. Archibald, J. L.; Beardsley, D. R.; Ward, T. J.; Waterfall, J. F.; White, J. F. J. Med. Chem. 1983, 26, 416.
31. (b) Klioze, S. S.; Ehrgott, F. J., Jr. J. Med. Chem. 1979, 22, 1497.
32. 3 revealed that 1 reacts much faster than 2b. (Compound 1 disappeared almost within 5 min, whereas a large amount of 2b remained unreacted.)
33. For chiral titanium(IV)-BINOL catalyzed enantioselective hetero Diels-Alder reaction, see also: (a) Mikami K.: Shimizu M. Chem. Rev. 1992, 92, 1021.
34. (b) Keck G. E.; Li X.-Y.; Krishnamurthy D. J. Org. Chem. 1995, 60, 5998.
35. The absolute configurations of the primary adduct and the final product (+)-4a have not been determined yet. Precise mechanistic studies on hetero Diels-Alder reactions of 2 including stereochemical information are in progress. In this communication, we have disclosed the first practical preparation of 2 and its hetero Diels-Alder reactions as an example of useful synthetic applications. Further applications of 2 for [4 + 2]-cyclo-addition with alkenes and reaction mechanisms will be described in a future full paper.