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.
Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis / Battaglia, Vincenzo; Meninno, Sara; Pellegrini, Andrea; Mazzanti, Andrea; Lattanzi, Alessandra. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 25:27(2023), pp. 5038-5043. [10.1021/acs.orglett.3c01736]
Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis
Pellegrini, Andrea;Mazzanti, Andrea;
2023
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.File | Dimensione | Formato | |
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