Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis.

ABSTRACT: An operationally simple Knoevenagel condensation/asymmetric epoxidation/domino ring-opening esterification (DROE) approach has been disclosed to successfully access a good variety of (R)- and (S)-α-arylglycine esters from commercially available aldehydes, phenylsulfonyl acetonitrile, cumyl hydroperoxide, anilines, and readily available Cinchona alkaloid-based catalysts using a single solvent and reaction vessel. DFT calculations performed on the key asymmetric epoxidation showed the importance of cooperative H-bonding interactions in affecting the stereocontrol.

SUBMITTER: Battaglia V 

PROVIDER: S-EPMC10353036 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature