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.

Battaglia, V., Meninno, S., Pellegrini, A., Mazzanti, A., Lattanzi, A. (2023). Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis. ORGANIC LETTERS, 25(27), 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.
2023
Battaglia, V., Meninno, S., Pellegrini, A., Mazzanti, A., Lattanzi, A. (2023). Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis. ORGANIC LETTERS, 25(27), 5038-5043 [10.1021/acs.orglett.3c01736].
Battaglia, Vincenzo; Meninno, Sara; Pellegrini, Andrea; Mazzanti, Andrea; Lattanzi, Alessandra
File in questo prodotto:
File Dimensione Formato  
battaglia-et-al-2023-single-flask-enantioselective-synthesis-of-α-amino-acid-esters-by-organocatalysis.pdf

accesso aperto

Tipo: Versione (PDF) editoriale
Licenza: Licenza per Accesso Aperto. Creative Commons Attribuzione (CCBY)
Dimensione 2.13 MB
Formato Adobe PDF
2.13 MB Adobe PDF Visualizza/Apri
ol3c01736_si_001.pdf

accesso aperto

Tipo: File Supplementare
Licenza: Licenza per Accesso Aperto. Creative Commons Attribuzione (CCBY)
Dimensione 12.19 MB
Formato Adobe PDF
12.19 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/959661
Citazioni
  • ???jsp.display-item.citation.pmc??? 1
  • Scopus 3
  • ???jsp.display-item.citation.isi??? 3
social impact