(R)-(+)-N-Methylbenzoguanidine ((R)-NMBG) catalyzed acylative kinetic resolution of racemic 3-hydroxy-3-aryl-propanoates. Issue 42 (19th October 2016) - Yamada, Akira
Graphical abstract: Highlights: The kinetic resolution of racemic β-hydroxy esters was achieved. ( R )-NMBG functioned as an efficient acyl transfer catalyst. The effect of the structure of the ester moiety was investigated. Cyclohexane carboxylic anhydride was a suitable acyl donor. Abstract: ( R )-(+)- N -methylbenzoguanidine (( R )-NMBG) functioned as an efficient acyl transfer catalyst for the acylative kinetic resolution of racemic β-hydroxy esters using cyclohexane carboxylic anhydride under mild reaction conditions. A tert -butyl ester moiety is necessary to achieve a high selectivity. The effects of the substituents on the aromatic rings of the substrates were systematically investigated, and diverse substrates participated in the reaction with good s -values (>20) irrespective of the type of substituents and their patterns, except for o -methoxy group.