Classical Kinetic Resolution of Racemic Alcohols

The establishment of suitable conditions for an irreversible equilibrium is of dramatic importance for the development of acylative KRs. To circumvent the problem of a possible undesired hydrolytic reverse reaction, the selection of an adequate acyl donor is crucial in order to drive the reaction to completion. For the acylation of alcohols, an acyl donor must be selected from a variety of esters, anhydrides, and carboxylic acids. Some revisions have been published in this field giving outstanding selection guides [47,48]. As mentioned before, the use of dry solvents is important to avoid hydrolytic side reactions, and also in some cases the use of MS has been described. 

A key aspect resides in the selection of a proper acyl donor, which activates the hydrolase forming the acyl-enzyme complex. In order to avoid the reversible 

9 ENANTIOSELECTIVE ACYLATION OF ALCOHOL AND AMINE REACTIONS IN ORGANIC SYNTHESIS 

General representation for the kinetic resoiution of racemic secondary aicohois. 

R =Me (vinyl acetate), Pr (vinyl butanoate), C9H19 (vinyl decanoate) 

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