(R)-(+)-N-Methylbenzoguanidine ((R)-NMBG) catalyzed acylative kinetic resolution of racemic 3-hydroxy-3-aryl-propanoates. Issue 42 (19th October 2016)

• Record Type: Journal Article
• Authors: Yamada, Akira; Nakata, Kenya
• Is Part Of: Tetrahedron letters. Volume 57:Issue 42(2016)
• Page Start: 4697
• Page End: 4701
• Publication Date: 2016-10-19
• Subjects: Kinetic resolution -- β-Hydroxy esters -- Organocatalysis -- N-Methylbenzoguanidine -- Acylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.09.014
• Languages: English
• ISSNs: 0040-4039

Abstract

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.