On the use of succinic anhydride as acylating agent for practical resolution of aryl–alkyl alcohols through lipase-catalyzed acylation

A comparison is carried out of the E-values recorded in the lipase-catalyzed resolution of a series of secondary aryl–alkyl alcohols with enol esters versus succinic anhydride. Whereas all the substrates could be resolved by a proper choice of the lipase/enol ester couple with moderate (E=50) to good (E>100) enantioselectivities, only some of them showed satisfactory enantioselectivity (E>50) with the use of succinic acid as acylating agent. Notably, indanol and 1-quinolin-3-yl-ethanol were resolved in a practical way, with E>100 and E>80, respectively.