α-Fluoro decalones as chiral epoxidation catalysts: Fluorine effect

Tetrahedron Asymmetry

Volumn 15, Issue 24, 2004, Pages 3891-3898

  Solladié Cavallo, Arlette ^a   Jierry, Loïc ^a   Klein, Arlette ^a   Schmitt, Michel ^a   Welter, Richard ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CARBONYL DERIVATIVE; FLUORINE; KETONE DERIVATIVE; STILBENE DERIVATIVE; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; EPOXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; THEORETICAL MODEL;

EID: 9944232534     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.10.033     Document Type: Article

References (31)

1. R. Mello, M. Fiorentino, C. Fusco, and C. Curci J. Am. Chem. Soc. 111 1989 6749
2. S.E. Denmark, Z. Wu, C.M. Crudden, and H.J. Matsuhashi J. Org. Chem. 62 1997 8288
3. A. Armstrong, and B.R. Hayter Chem. Commun. 1998 621 622
4. Y. Tu, Z.X. Wang, M. Frohn, M. He, H. Yu, Y. Tang, and Y. Shi J. Org. Chem. 63 1998 8475
5. D. Yang, Y.C. Yip, Chen, and K.K. Cheung J. Am. Chem. Soc. 120 1998 7659 7660
6. S.E. Denmark, and Z. Wu Synlett 1999 847
7. A. Solladié-Cavallo, and L. Bouérat Org. Lett. 2 2000 3531 3534
8. A. Solladié-Cavallo, L. Jierry, H. Norrousi-Arasi, and D. Tahmassebi J. Fluorine Chem. 125 2004 1371 1377
9. A. Armstrong, W.O. Moss, and J.R. Reeves Tetrahedron: Asymmetry 12 2001 2779
10. A. Armstrong, G. Ahmed, B. Dominguez-Fernandez, B.R. Hayter, and J.S. Wailes J. Org. Chem. 67 2002 8610
11. S.E. Denmark, and H. Matsuhashi J. Org. Chem. 67 2002 3479
12. C.J. Stearman, and V. Behar Tetrahedron Lett. 43 2002 1943
13. S. Klein, and S.M. Roberts J. Chem. Soc. Perkin Trans. 1 19 2002 2686
14. A. Solladié-Cavallo, L. Bouérat, and L. Jierry Eur. J. Org. Chem. 2001 4557 4560
15. The corresponding epoxide is a key intermediate in the synthesis of hypotensive drugs, such as diltiazem, clentiaezm and naltiazem
16. F. Toda, and K. Tanaka Tetrahedron Lett. 29 1988 551 554
17. 3 to form the desired decalone. In our case the decalol was minor and a separation was prefered
18. G. Di Maio, L.M. Migneco, E. Vecchi, and C. Lavarone Magn. Resn. Chem. 38 2000 108
19. E. Piers, R.W. Britton, and W. De Waal Can. J. Chem. 47 1969 831 For the dehydration step these authors obtained only isomer 10, while we got a 9/1 mixture of 10 and 11
20. Quantitative yield of silylenolate was obtained after modification of the literature work-up: no addition of water at all, cf.: A. Solladié- Cavallo, L. Jierry, L. Bouérat, and P. Taillasson Tetrahedron: Asymmetry 12 2001 883 891
21. Milan Balaz, PhD dissertation, Strasbourg, June 2003
22. A. Solladié-Cavallo, L. Jierry, L. Bouérat, and P. Taillasson Tetrahedron: Asymmetry 12 2001 883
23. A. Solladié-Cavallo, L. Jierry, L. Bouérat, and M. Schmitt Tetrahedron 58 2002 4195
24. For assignment of the (+)-(R,R) configuration of the stilbene oxide, see: M. Imuta, and H. Ziffer J. Org. Chem. 44 1979 2505
25. For the assignment of (+)-(2S,3R)-configuration to the methyl p-methoxycinnamate epoxide, see: K. Matsuki, M. Sobukawa, A. Kawai, H. Inoue, and M. Takeda Chem. Pharm. Bull. 41 1993 643 (+)-(R,R)- and (-)-(S,S)-β- methylstyrene oxide are commercially available: cf. Aldrich Chiral catalogue
26. A. Armstrong, I. Washington, and K.N. Houk J. Am. Chem. Soc. 122 2000 6297
27. A.L. Baumstark, and C.J. McKloskey Tetrahedron Lett. 28 1987 3311
28. D. Yang, X.C. Wang, M.K. Wong, Y.C. Yip, and M.W. Tang J. Am. Chem. Soc. 118 1996 11311
29. W. Adam, R. Paredes, A.K. Smerz, and L.A. Veloza Liebigs Ann. 1997 547
30. C. Jenson, J. Liu, K.N. Houk, and W.L. Jorgensen J. Am. Chem. Soc. 119 1997 12982
31. Direct epoxidation by oxone provided some of the racemic epoxide, which thus lowered the enantioselectivity observed. However there is a direct epoxidation but with β-methylstyrene