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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

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

Battaglia Vincenzo V Meninno Sara S Pellegrini Andrea A Mazzanti Andrea A Lattanzi Alessandra A

Organic letters 20230629 27

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 sh ...[more]

PMID: 37382588

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