Enzymatic resolution of N-protected-β3-amino methyl esters, using lipase B from Candida antarctica

Structural features of N-benzylated-β-amino acid methyl esters essential for enantiodifferentiation by lipase B from Candida antarctica in hydrolytic reactions

“…In this regard, our group previously reported the kinetic resolution of racemic N-protected-b 3 -amino acid methyl esters through transesterifications catalyzed by lipase B from Candida antarctica (CALB). 12 More recently, Forró and Fülöp published an excellent compilation of lipase-catalyzed hydrolytic methods for the preparation of enantiomerically pure b-amino acids, 13 many of which involve the use of CALB to carry out enantioselective hydrolysis of b-lactams and carbocyclic b-amino acid esters. However, lack of methodologies based on CALB-catalyzed enantioselective hydrolysis of acyclic b-amino acid esters drew our attention.…”

An efficient new enzymatic method for the preparation of β-aryl-β-amino acid enantiomers

“…1 There are several methods for the synthesis of enantiopure b-aryl-b-amino acids, such as (i) the enantioselective reduction of a b-enamino ester; 2 (ii) the addition of a chiral sulfoxide to a substituted N-sulfonylimine; 3 (iii) an asymmetric catalytic Mannich reaction; 4 (iv) the conjugate addition of a chiral lithium amide to a b-aryl a,b-unsaturated ester; 5 (v) the reaction of a Reformatsky reagent with an imine; 6 or (vi) the preparation of a diastereomeric salt. 7 In addition to asymmetric synthetic routes, 2-7 enzyme-catalysed processes have been developed through (i) the transesterification of an N-protected ester in isobutanol; 8 (ii) stereoselective degradation of a racemic amino acid; 9 (iii) hydrolysis of a racemic b-amino ester; 10 (iv) hydrolysis of a racemic N-acetylated b-amino acid; 11 or (v) an aminomutasecatalysed a,b-rearrangement 12 in aqueous medium.…”

Enzymatic Aminolysis and Ammonolysis Processes in the Preparation of Chiral Nitrogenated Compounds

“…These compounds can be easily prepared in its racemic form, and it is possible to carry out a biocatalytic resolution by acylation of the amino group, or by hydrolysis, transesterification or aminolysis through the ester function. The bioresolution of aromatic β-aminoesters via enzymatic hydrolysis has been carried out [67] and this methodology has been most exhaustively used than acylation of amino group or aminolysis of the ester, for instance, racemic β-aminobutyrate esters bearing the amino function protected have been resolved by enantioespecific transesterification with butanol and CALB as biocatalyst [68]. It seems that the resolution by acylation of amino group Scheme 25.…”