Asymmetric organocatalysis of epoxidation by iminium salts under non-aqueous conditions

Tetrahedron

Volumn 63, Issue 25, 2007, Pages 5386-5393

  Page, Philip C Bulman ^a   Buckley, Benjamin R ^a   Barros, David ^a   Blacker, A John ^a,b   Marples, Brian A ^a   Elsegood, Mark R J ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b NPIL Pharmaceuticals (UK) Ltd   (United Kingdom)

Author keywords

Catalysis; Epoxidation; Homogeneous; Organocatalysis

Indexed keywords

ALKENE DERIVATIVE; IMINE; PHOSPHONIUM DERIVATIVE; SODIUM CHLORIDE; SOLVENT; TETRAPHENYLPHOSPHONIUM PEROXYBISULFATE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; ENANTIOMER; EPOXIDATION; NONAQUEOUS PHASE LIQUID; PRIORITY JOURNAL; STOICHIOMETRY; TEMPERATURE;

EID: 34248631965     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.04.066     Document Type: Article

References (37)

1. Hanquet G., Lusinchi X., and Milliet P. Tetrahedron Lett. 28 (1987) 6061
2. Hanquet G., Lusinchi X., and Milliet P. Tetrahedron Lett. 29 (1988) 3941
3. Bohé L., Hanquet G., Lusinchi M., and Lusinchi X. Tetrahedron Lett. 34 (1993) 7271
4. Bohé L., Lusinchi M., and Lusinchi X. Tetrahedron 55 (1999) 141
5. Picot A., Millet P., and Lusinchi X. Tetrahedron Lett. 17 (1976) 1573
6. Aggarwal V.K., and Wang M.F. Chem. Commun. (1996) 191
7. Armstrong A., Ahmed G., Garnett I., and Gioacolou K. Synlett (1997) 1075
8. Armstrong A., Ahmed G., Garnett I., Gioacolou K., and Wailes J.S. Tetrahedron 55 (1999) 2341
9. Bohé L., and Kammoun M. Tetrahedron Lett. 43 (2002) 803
10. Gluszynska A., Mackowska I., Rozwadowska M.D., and Sienniak W. Tetrahedron: Asymmetry 15 (2004) 2499
11. Biscoe M.R., and Breslow R. J. Am. Chem. Soc. 127 (2005) 10812
12. Armstrong A., and Draffan A.G. Synlett (1998) 646
13. Armstrong A., and Draffan A.G. Tetrahedron Lett. 40 (1999) 4453
14. Armstrong A., and Draffan A.G. J. Chem. Soc., Perkin Trans. 1 (2001) 2861
15. Minakata S., Takemiya A., Nakamura K., Ryu I., and Komatsu M. Synlett (2000) 1810
16. Wong M.-K., Ho L.-M., Zheng Y.-S., Ho C.-Y., and Yang D. Org. Lett. 16 (2001) 2587
17. Page P.C.B., Rassias G.A., Bethell D., and Schilling M.B. J. Chem. Soc., Perkin Trans. 1 (2000) 3325
18. Page P.C.B., Rassias G.A., Barros D., Ardakani A., Buckley B., Bethell D., Smith T.A.D., and Slawin A.M.Z. J. Org. Chem. 66 (2001) 6926
19. Page P.C.B., Rassias G.A., Barros D., Ardakani A., Bethell D., and Merrifield E. Synlett (2002) 580
20. Page P.C.B., Buckley B.R., and Blacker A.J. Org. Lett. 6 (2004) 1543
21. Page P.C.B., Buckley B.R., Appleby L.F., and Alsters P.A. Synthesis (2005) 3405
22. Page P.C.B., Buckley B.R., Rassias G.A., and Blacker A.J. Eur. J. Org. Chem. (2006) 803
23. 2). Absolute structure parameter -0.06(13), thus well determined. Four cations, four anions and a molecule of dichloromethane in the asymmetric unit. The four cations have almost identical conformations.
24. Lacour J., Monchaud D., and Marsol C. Tetrahedron Lett. 43 (2002) 8257
25. Vachon J., Pérollier C., Monchaud D., Marsol C., Ditrich K., and Lacour J. J. Org. Chem. 70 (2005) 5903
26. Gonçalves M.-H., Martinez A., Grass S., Page P.C.B., and Lacour J. Tetrahedron Lett. 47 (2006) 5297
27. Vachon J., Rentsch S., Martinez A., Marsol C., and Lacour J. Org. Biomol. Chem. 5 (2007) 501
28. Campestrini S., Di Furia F., Labat G., and Novello F. J. Chem. Soc., Perkin Trans. 2 (1994) 2175
29. Page P.C.B., Barros D., Buckley B.R., Ardakani A., and Marples B.A. J. Org. Chem. 69 (2004) 3595
30. Page P.C.B., Barros D., Buckley B.R., and Marples B.A. Tetrahedron: Asymmetry 16 (2005) 3488
31. Page P.C.B., Buckley B.R., Heaney H., and Blacker A.J. Org. Lett. 7 (2005) 375
32. Page P.C.B., Buckley B.R., Barros D., Heaney H., Blacker A.J., and Marples B.A. Tetrahedron 62 (2006) 6607
33. Unpublished results.
34. Berti G., Macchia B., Macchia F., and Monti L. J. Org. Chem. 33 (1968) 4045
35. Chang H.-T., and Sharpless K.B. J. Org. Chem. 61 (1996) 6456
36. Tian H., She X., Shu L., Yu H., and Shi Y. J. Am. Chem. Soc. 122 (2000) 11551
37. Padwa A., and Owens D. J. Org. Chem. 42 (1977) 3076