Acylative kinetic resolution of racemic aromatic β-hydroxy esters catalyzed by chiral nucleophilic N-(1-arylethyl)benzoguanidines. Issue 4 (15th April 2017)

• Record Type: Journal Article
• Authors: Yamada, Akira; Nakata, Kenya; Shiina, Isamu
• Is Part Of: Tetrahedron, asymmetry. Volume 28:Issue 4(2017)
• Page Start: 516
• Page End: 521
• Publication Date: 2017-04-15
• Subjects: Asymmetry (Chemistry) -- Periodicals; 547.005
• DOI: 10.1016/j.tetasy.2017.03.005
• Languages: English
• ISSNs: 0957-4166

Abstract

Graphical abstract: Abstract: An efficient acylative kinetic resolution of racemic aromatic β-hydroxy esters with cyclohexanecarboxylic anhydride was achieved using newly designed ( R )- N -methylbenzoguanidine (( R )-NMBG) derivatives. A series of ( R )-NMBG derivatives was synthesized by modifying the original ( R )-NMBG catalyst with the introduction of branched N -substituents containing a stereogenic center, and their catalytic performance was evaluated. ( R, R )- N -(1-(β-1-Naphthyl)ethyl)benzoguanidine [( R, R )-NβNpEtBG] was found to function as an efficient acyl transfer catalyst for the reaction of a broad variety of substrates, regardless of the substituent type and substitution pattern.