1308372-75-9Relevant academic research and scientific papers
Kinetic resolution of the racemic 1-(aryloxazol-2-YL)carbinols with achiral carboxylic acids by asymmetric esterification: A new method for the preparation of chiral 1,2-amino alcohols
Nakata, Kenya,Ono, Keisuke,Shiina, Isamu
scheme or table, p. 1171 - 1180 (2011/05/14)
An efficient kinetic resolution of racemic 1-(aryloxazol-2-yl)carbinols with achiral carboxylic acids using pivalic anhydride in the presence of (R)-benzotetramisole ((R)-BTM) is reported. It was determined that the naphth[1,2-d]oxazole moiety at the C-1 position in the alcohols is a suitable structure to attain a high selectivity. An application to produce optically pure 1,2-amino alcohols was developed by the kinetic resolution of the racemic 1-(aryloxazol-2-yl)carbinols followed by a two-step cleavage of the aryloxazole part to form the corresponding amino group. Transition states that provide the desired (R)-esters from (R)-1-(benzoxazol-2-yl)ethan-1-ol or the undesired (S)-esters from (S)-1-(benzoxazol-2-yl)ethan-1-ol are disclosed by DFT calculations. Another transition state that affords the desired (R)-ester from (R)-1-(naphth[1,2-d]oxazol-2-yl)ethan-1-ol included in the racemic mixture is also estimated, and the structural features of these transition states are discussed. The Japan Institute of Heterocyclic Chemistry.
