DOI: 10.1039/A905594K
(Paper)
Reference Section for: Chem. Commun., 1999, 1787-1788
The first efficient bovine serum albumin catalyzed asymmetric oxidation of tertiary amines to the corresponding N-oxides via kinetic dynamic resolution
(Note: The full text of this document is currently only available in the PDF Version )
Stefano Colonna, Nicoletta Gaggero, Józef Drabowicz, Piotr Łyżwa and Marian Mikołajczyk
Abstract
Unsymmetrical teriary amines were oxidized with a few oxidants in the presence of bovine serum albumin to give the corresponding N-oxides of the highest optical purity ever reported (up to 66%) for the reaction of asymmetric oxidation of amines via their kinetic dynamic resolution.
References
- M. Mikołajczyk, J. Drabowicz and P. Kiełbasiński, Chiral Sulfur Reagents: Application in Asymmetric and Stereoselective Synthesis, CRC Press, Boca Raton, 1997 Search PubMed.
- M. K. Pietrusiewicz and M. Zabłocka, Chem. Rev., 1994, 94, 1375 CrossRef.
- F. A. Davis and J. R. H. Jenkins, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, New York, 1983, vol. 4, pp. 346–351 Search PubMed.
- J. Meisenheimer, Chem. Ber., 1908, 41, 3966 Search PubMed; J. Meisenheimer, Ann., 1928, 428, 252 Search PubMed.
- G. Berti and G. Belluci, Tetrahedron Lett., 1964, 3853 CrossRef CAS.
- S. Goldberg and F. L. Lam, J. Am. Chem. Soc., 1969, 94, 5113 CrossRef.
- F. Toda, K. Mori, Z. Stein and I. Goldberg, Tetrahedron Lett., 1989, 30, 1841 CrossRef CAS.
- M. R. Hadley, E. Śvidlenka, L. A. Damani, H. G. Oldham, J. Tribe, P. Camilleri and A. J. Hutt, Chirality, 1994, 6, 91 CAS.
- J. D. Morrison, K. P. Long, unpublished results cited in J. D. Morrison and H. S. Mosher, Asymmetric Organic Reactions, ACS, Washington, p. 367 Search PubMed.
- K. Lang, Diss. Abstr. Int. B, 1970, 31, 3926 Search PubMed.
- M. Moriwaki, Y. Yamamoto, J. Oda and Y. Inonye, J. Org. Chem., 1976, 41, 300 CrossRef CAS.
- (a) S. Colonna, S. Banfi, R. Annunziata and L. Casella, J. Org. Chem., 1986, 51, 891 CrossRef CAS; (b) S. Colonna, N. Gaggero, M. Leone and P. Pasta, Tetrahedron, 1991, 47, 8385 CrossRef CAS; (c) M. Chiari, C. Ettori, P. G. Righetti, S. Colonna, N. Gaggero and A. Negri, Electrophoresis, 1991, 12, 376 CAS.
- For a recent application of the dynamic kinetic resolution strategy to asymmetric conversions, see M. M. Jones and J. M. J. Williams, Chem. Commun., 1998, 2519 Search PubMed.
- U. Krugah-Hansen, Pharmacol. Rev., 1981, 33, 17 Search PubMed.
- J. Drabowicz, B. Dudiński, M. Mikołajczyk, S. Colonna and N. Gaggero, Tetrahedron: Asymmetry, 1997, 8, 2267 CrossRef CAS.