Avoid racemization! Short lipophilic oligopeptides utilizing nucleophilic N-π-methyl histidine residues catalyze the desymmetrization of meso-1,2-diols with enantiomeric ratios of up to 94:6. Direct one-pot oxidation, which avoids the well-known racemization of the monoacylated product, directly leads to α-acetoxy ketones with enantiomeric ratios of up to 97:3 and 97 % yield.
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Zell et al. (2009) studied this question.
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