Study On Knetie Resolution And Dynamic Knetie Resolution Of Propargylic Alcohols

Chiral propargylic alcohols are among the most versatile synthetic materials as they bear a hydroxyl group and an propargylic group on one chiral carbon. A series of bio-active compounds such as eicosanoids, macrolides and enediyne antibiotics were enantio-selectively prepared with optically active propargylic alcohols as important intermediates.Following by our previous investigation in the kinetic resolution of cyanohydrins and allylic alcohols catalyzed by the lipase, we are now investigating the stereoselective preparation of propargylic alcohols catalyzed by enzyme.By using lipase PS-30as catalyst, By using lipase PS-30as catalyst, the kinetic resolution of a series of racemic propargylic alcohols has been achieved via stereoselective acylation. Under optimizing reaction conditions, good enantiselectivities can be achieved for most of the investigated compounds. The value of kinetic enantiomeric ratio (E) reached up to139. Substituent effect is briefly discussed.The influence of substrate structure, steric and electronic nature and position of the aryl ring substituent on the enantioselectivity is discussed.