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. 2003 Jun 25;125(25):7490-1.
doi: 10.1021/ja0300315.

Is it possible to estimate the enantioselectivity of a chiral catalyst from its racemic mixture?

Franz Lagasse  1 , Masaki Tsukamoto, Christopher J Welch, Henri B Kagan
Affiliations

Is it possible to estimate the enantioselectivity of a chiral catalyst from its racemic mixture?

Franz Lagasse et al. J Am Chem Soc. .

Abstract

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.

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