Is It Possible To Estimate the Enantioselectivity of a Chiral Catalyst from Its Racemic Mixture?

Autor:	Masaki Tsukamoto, Christopher J. Welch, Henri B. Kagan, Franz Lagasse
Rok vydání:	2003
Předmět:	chemistry.chemical_classification Ketone Diol Homogeneous catalysis General Chemistry Borane Biochemistry Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Enantiopure drug chemistry Racemic mixture Organic chemistry Enantiomer
Zdroj:	Journal of the American Chemical Society. 125:7490-7491
ISSN:	1520-5126 0002-7863
Popis:	The evaluation of a racemic catalyst was investigated in the case of oxazaborolidine (OAB)-catalyzed borane reduction of 1,5-diphenyl-1,5-pentanedione, giving the corresponding diol. On the basis of the diastereoselectivity of the diols, it is possible to estimate the enantioselectivity (ee) of the first step, which correlates well with the ee in the reaction of the structurally similar phenyl n-pentyl ketone with enantiopure OAB catalyst. The measure of diastereoselectivity could be a tool for screening racemic catalysts without the need for resolving the individual enantiomers, if in the second step of the process there is no substrate control and no catalyst scrambling.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ec02c5529305a6c2f7d12d90bb9000ec https://doi.org/10.1021/ja0300315 Zobrazit plný text záznamu