Asymmetric epoxidation of trans-olefins via chiral dioxiranes: A possible contribution of axial approaches in the case of tri- and tetrasubstituted α-fluoro cyclohexanones

European Journal of Organic Chemistry

Volumn , Issue 23, 2001, Pages 4557-4560

  Solladié Cavallo, Arlette ^a   Bouérat, Laëtitia ^a   Jierry, Loïc ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Alkenes; Asymmetric synthesis; Chirality; Epoxidation

Indexed keywords

ALKENE; CYCLOHEXANONE; ETHYLENE OXIDE; STILBENE;

ANALYTIC METHOD; ARTICLE; CHIRALITY; CIRCULAR DICHROISM; ENANTIOMER; EPOXIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0035215391     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200112)2001:23<4557::aid-ejoc4557>3.3.co;2-1     Document Type: Article

References (23)

1. A. Solladié-Cavallo, L. Bouérat, Org. Lett. 2000, 2, 3531-3534.
2. For the synthesis and characterization of ketones 1a, 1e, 2a and 2e, see: A. Solladié-Cavallo, L. Bouérat, Tetrahedron: Asymmetry 2000, 11, 935.
3. D. Yang, Y. C. Yip, J. Chen, K. K. Cheung, J. Am. Chem. Soc. 1998, 120, 7659-7660.
4. A. Solladié-Cavallo, L. Bouerat, L. Jierry, P. Taillasson, Tetrahedron: Asymmetry 2001, 12, 883.
5. X. Cao, T. B. Freedman, L. Nafié, A. Solladié-Cavallo, L. Jierry, L. Bouérat, (submitted).
6. This result (equatorial phenyl-axial methyl at C-5) is not in opposition with Eliel's results (E. L. Eliel, M. Manoharan, J. Org. Chem. 1981, 46, 1959
7. Stereochemistry of Organic Compounds, Eliel/Wilen/Mander, John Wiley & Sons, Inc., 1994, p. 706) which concern only phenyl-methyl-disubstituted cyclohexane. In this case, we are dealing with tetrasubstituted compounds and with α-disubstituted cyclohexanones where a fluorine atom and a methyl group are in competition. It is known that, depending on the solvent, a fluorine atom α to a carbonyl may slightly prefer the equatorial position but that a methyl group áto a carbonyl significantly prefers the equatorial position.
8. Moreover, hyperconjugative σ*,π-interactions between the carbonyl and the axial C-halogen (C-F) or C-C (C-Me) bond are present (cf. E. J. Corey, H. J. Burke, J. Am. Chem. Soc. 1955, 77, 5418
9. Stereochemistry of Organic Compounds, Eliel/Wilen/Mander, John Wiley & Sons, Inc., 1994, p. 732-733).
10. For epoxidation of unsubstituted ethyl cinnamate with a ketone having tropane and/or cyclohexane skeletons see: A. Armstrong, B. R. Hayter, Chem. Commun. 1998, 621-622;
11. Z. X. Wang, Y. Tu, M. Frohn, J. R. Zhang, Y. Shi, J. Am. Chem. Soc. 1997, 119, 11224;
12. Z. X. Wang, S. M. Miller, O. P. Anderson, Y. Shi, J. Org. Chem. 1999, 64, 6443-6458;
13. W. Adam, C. R. Saha-Möller, C. G. Zhao, Tetrahedron: Asymmetry 1999, 10, 2749-2755.
14. For assignment of the (-)-(S,S) configuration to the stilbene oxide, see: M. Imuta, H. Ziffer, J. Org. Chem. 1979, 44, 2505-2509.
15. For assignment of the (-)-(2R,3S) configuration to the methyl p-methoxy cinnamate epoxide, see: K. Matsuki, M. Sobukawa, A. Kawai, H. Inoue, M. Takeda, Chem. Pharm. Bull. 1993, 41, 643-648.
16. A. L. Baumstark, C. J. McKloskey, Tetrahedron Lett. 1987, 28, 3311.
17. [9a] W. Adam, R. Paredes, A. K. Smerz, L. A. Veloza, Liebigs Ann./Recueil 1997, 547;
18. [9b] K. N. Houk, J. Liu, N. C. DeMello, K. R. Condroski, J. Am. Chem. Soc. 1997, 119, 10147.
19. [10a] C. Jenson, J. Liu, K. N. Houk, W. L. Jorgensen, J. Am. Chem. Soc. 1997, 119, 12982;
20. [10b] R. D. Bach, J. L. Andres, A. L. Owensby, H. B. Schlegel, J. J. W. McDouall, J. Am. Chem. Soc. 1992, 114, 7207.
21. A. Armstrong, I. Washington, K. N. Houk, J. Am. Chem. Soc. 2000, 122, 6297-6298.
22. A. Solladié-Cavallo, A. Diep-Vohuule, V. Sunjic, V. Vinkovic, Tetrahedron: Asymmetry 1996, 7, 1783.
23. L. Zard, A. Tixidre, A. Wick, FR 2 672 600, A1 (Synthelabo, France), 1991.