Crystallization-Induced Dynamic Resolution CIDR

It is hoped that the nomenclature itself will resolve. 

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Oxazolidine 198 was produced from condensation of (R)-phenylg-lycinol and fluoral ethyl hemiacetal as a 62 38 tram/cis diastereomeric mixture. The enantiopure trans-198 was obtained through an epimeriza-tion with p-toluenesulfonic acid that realized the selective precipitation of the desired diastereoisomer. The repetition of this crystallization-induced dynamic resolution (CIDR) protocol on mother liquors allowed an almost complete conversion of the initial mixture into the desired trans-198. This chiral oxazolidine was used as chiral auxiliary for the synthesis of a-fluorocarboxylic acids and P-fluoroalcohols in a one-pot procedure that also allowed its recovery without loss of optical purity (13JOC3487). 

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