Chiral unsaturated alcohols are often used as intermediates in asymmetric synthesis. Kinetic resolution of racemic 1-arylallyl and 1-arylpropargyl esters via lipase-catalyzed enantioselective hydrolysis and alcoholysis afforded corresponding (R)-alcohols were obtained with excellent ee (98-100 %). To achieve DKR of the same unsaturated racemic esters, we investigated Pd, Ir, Rh, In, and Cu complexes as racemization catalysts. In our iridium-lipase DKR system, racemic allylic acetates were successfully converted into chiral alcohols in good yields and excellent ee (95-100 %). 

Chemoenzymatic dynamic kinetic resolution of unsaturated esters via transition-metal-catalyzed racemization and lipase-catalyzed hydrolysis or alcoholysis

245th National Meeting (2013)

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