On June 30, 2000, Bew, Sean P.; Davies, Stephen G.; Fukuzawa, Shin-Ichi published an article.COA of Formula: C8H15NO2 The title of the article was Kinetic resolution of α-acetoxy carboxylic acids with homochiral SuperQuats. And the article contained the following:
Preliminary investigations focused on the kinetic resolution of (±)-O-acetyl mandelic acid chloride with iso-Pr SuperQuat and iso-Pr Evans’ homochiral auxiliaries. The addition of 2 equiv of the acid chloride to the lithium salts of the auxiliaries (SuperQuat and Evans’) at -100° in THF afforded the N-acyl auxiliaries in high chem. yields (95 and 89%) and d.e.’s of 66 and 40%, resp. Using the same mandelic acid chloride but incorporating SuperQuat auxiliaries derived from (S)-phenylglycine and (S)-phenylalanine gave the N-acyl SuperQuats in 86 and 90% yield and d.e.’s of 66 and 30%, resp. Replacing the Ph group in the O-acetyl mandelic acid chloride with a Bu, tert-Bu, or cyclohexyl group changed the d.e. significantly when kinetically resolved with iso-Pr SuperQuat. The yields were all similar, i.e., ∼90%, but the d.e.’s varied considerably, with values of 20, 50, and 82%, resp. Attempted kinetic resolution of α-methoxy-phenylacetyl chloride using the lithium salt of iso-Pr SuperQuat revealed a diastereoselectivity of 45%, significantly lower than that obtained with the corresponding α-acetoxy carboxylic acid chlorides. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).COA of Formula: C8H15NO2
The Article related to acetoxy acid chloride kinetic resolution superquat, Heterocyclic Compounds (More Than One Hetero Atom): Oxazoles, Isoxazoles and other aspects.COA of Formula: C8H15NO2
Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem