Effect of the medium on the oxaziridinium-catalyzed enantioselective epoxidation

Tetrahedron Letters

Volumn 43, Issue 46, 2002, Pages 8257-8260

  Lacour, Jerome ^a   Monchaud, David ^a   Marsol, Claire ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; IMINE; OXAZIRIDINE DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; EPOXIDATION; OXYGEN TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037064522     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02025-7     Document Type: Article

References (32)

1. Jacobsen E.N., Wu M.H. Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. 2:1999;649 Springer-Verlag, Berlin.
2. Bonini C., Righi G. Tetrahedron. 58:2002;4981-5021.
3. Porter M.J., Skidmore J. Chem. Commun. 2000;1215-1225.
4. Denmark S.E., Wu Z.C. Synlett. 1999;847-859.
5. Lusinchi X., Hanquet G. Tetrahedron. 53:1997;13727-13738.
6. Adam W., Saha-Moller C.R., Ganeshpure P.A. Chem. Rev. 101:2001;3499-3548.
7. Bohé L., Lusinchi M., Lusinchi X. Tetrahedron. 55:1999;141-154.
8. Aggarwal V.K., Wang M.F. Chem. Commun. 1996;191-192.
9. Page P.C.B., Rassias G.A., Barros D., Ardakani A., Buckley B., Bethell D., Smith T.A.D., Slawin A.M.Z. J. Org. Chem. 66:2001;6926-6931.
10. Armstrong A., Ahmed G., Garnett I., Goacolou K., Wailes J.S. Tetrahedron. 55:1999;2341-2352.
11. Minakata S., Takemiya A., Nakamura K., Ryu I., Komatsu M. Synlett. 2000;1810-1812.
12. Wong M.K., Ho L.M., Zheng Y.S., Ho C.Y., Yang D. Org. Lett. 3:2001;2587-2590.
13. To the noticeable exception of some olefins, see: Aggarwal, V. K. WO. 9 706 147, 1997.
14. Page P.C.B., Rassias G.A., Barros D., Ardakani A., Bethell D., Merifield E. Synlett. 2002;580-582.
15. Armstrong A., Draffan A.G. J. Chem. Soc., Perkin Trans. 1. 2001;2861-2873.
16. Washington I., Houk K.N. J. Am. Chem. Soc. 122:2000;2948-2949.
17. Lacour J., Ginglinger C., Favarger F. Tetrahedron Lett. 1998;4825-4828.
18. Lacour J., Ginglinger C., Grivet C., Bernardinelli G. Angew. Chem., Int. Ed. Engl. 36:1997;608-609.
19. Lacour J., Jodry J.J., Monchaud D. Chem. Commun. 2001;2302-2303. and references cited therein.
20. This property has led to successful applications of 1 as a chiral selector in asymmetric extraction processes: Lacour, J.; Goujon-Ginglinger, C.; Torche-Haldimann, S.; Jodry, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695-3697; Jodry, J. J.; Lacour, J. Chem. Eur. J. 2000, 6, 4297-4304.
21. This property has led to successful applications of 1 as a chiral selector in asymmetric extraction processes: Lacour, J.; Goujon-Ginglinger, C.; Torche-Haldimann, S.; Jodry, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695-3697; Jodry, J. J.; Lacour, J. Chem. Eur. J. 2000, 6, 4297-4304.
22. Ooi T., Uematsu Y., Kameda M., Maruoka K. Angew. Chem., Int. Ed. 41:2002;1551-1554. and references cited therein.
23. 2-symmetric organic cations, although in practice, low induction is usually observed: Lacour, J.; Londez, A.; Goujon-Ginglinger, C.; Buß, V.; Bernardinelli, G. Org. Lett. 2000, 2, 4185-4188; Pasquini, C.; Desvergnes-Breuil, V.; Jodry, J. J.; Dalla Cort, A.; Lacour, J. Tetrahedron Lett. 2002, 43, 423-426 and this paper.
24. 2-symmetric organic cations, although in practice, low induction is usually observed: Lacour, J.; Londez, A.; Goujon-Ginglinger, C.; Buß, V.; Bernardinelli, G. Org. Lett. 2000, 2, 4185-4188; Pasquini, C.; Desvergnes-Breuil, V.; Jodry, J. J.; Dalla Cort, A.; Lacour, J. Tetrahedron Lett. 2002, 43, 423-426 and this paper.
25. Large scale preparation of 3 was realized by ozonolysis of phenanthrene: Agranat I., Rabinovitz M., Shaw W.-C. J. Org. Chem. 44:1979;1936-1941.
26. To simplify the denomination of the chiral entities, symbols L and D were maintained for 2a and 4a; L and D meaning configurations (4S,5S) and (4R,5R) for the acetonamine moiety, respectively.
27. Leonard N.J., Leubner G.W. J. Am. Chem. Soc. 71:1949;3408-3411.
28. 3NH][Λ-1] (e.r. >39:1) and [cinchonidinium][Δ?1] (d.r. >39:1) were used for the anion-exchange reactions.
29. Reichardt C. Solvents and Solvent Effects in Organic Chemistry. 2nd ed. 1988;VCH, Weinheim.
30. This result is confirmed by the lack of asymmetric induction in the reaction of 5 with precatalyst [2b][Δ-1] under homogenous polar conditions ( Table 1, entry 3).
31. 3) were performed and showed at 253 K, a 1.8:1 ratio of signals for diastereomeric (aS) and (aR) conformations, and this for both [L-2a][Λ-1] and [L-2a][Δ-1] salts. For compound [2b][Δ-1], no induction was observed.
32. This inversion in the sense of configuration might be the explanation for the decrease in selectivity in the enantioselective epoxidation of acyclic 8, compound 8 being structurally related to 6.