Observation and quantification of a chiral medium induced difference in rate of enantiomerization

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Kai Rossen, Jess Sager and Yongkui Sun


Abstract

A chiral stationary phase HPLC column has been used both to separate the enantiomers of a γ-lactol and also to observe the rate of enantiomerization of the individual enantiomers; the rate of enantiomerization differed for both enantiomers in the presence of the chiral stationary phase.


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