Organocatalytic Kinetic Resolution of Propargylic Alcohols

Significance A Lewis base catalyzed kinetic resolution of propargylic alcohols has been developed. Acylation of racemic secondary alcohols 1 in the presence of propionic anhydride and 4 mol% of chiral benzotetramisole (BTM) 2 provides enantioenriched products of type 3 and 4 with selectivity factors of up to 32. Linear and branched alkyl substrates as well as aryl precursors can be used.