The field of organocatalysis is expanding at a fast pace. Its growth is sustained by major stimuli, such as the effort toward an understanding of the mechanisms of reaction and catalytic processes in general, the elucidation of basic properties leading to stereocontrol and the search for broad applicability and scalability of the synthetic methodology. This paper reports a thorough study based on ESI-MS spectrometry of amino-organocatalyzed model reactions under different experimental conditions. Off-line reaction monitoring of mixtures containing different catalytic systems, by ESI-MSn showed the presence of several putative intermediate species, either in their protonated or sodiated forms. In addition, enantioselective chromatography of crude reactions provides the stereochemical outcome of asymmetric reactions. The bulk of the data collected offers a clue of the intricate pathways occurring in solution for the studied reactions.

Primary amine catalyzed activation of carbonyl compounds: a study on reaction pathways and reactive intermediates by mass spectrometry / Iazzetti, A.; Mazzoccanti, G.; Bencivenni, G.; Righi, P.; Calcaterra, A.; Villani, C.; Ciogli, A.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2022:3(2022). [10.1002/ejoc.202101272]

Primary amine catalyzed activation of carbonyl compounds: a study on reaction pathways and reactive intermediates by mass spectrometry

Iazzetti A.;Mazzoccanti G.;Calcaterra A.;Villani C.;Ciogli A.
2022

Abstract

The field of organocatalysis is expanding at a fast pace. Its growth is sustained by major stimuli, such as the effort toward an understanding of the mechanisms of reaction and catalytic processes in general, the elucidation of basic properties leading to stereocontrol and the search for broad applicability and scalability of the synthetic methodology. This paper reports a thorough study based on ESI-MS spectrometry of amino-organocatalyzed model reactions under different experimental conditions. Off-line reaction monitoring of mixtures containing different catalytic systems, by ESI-MSn showed the presence of several putative intermediate species, either in their protonated or sodiated forms. In addition, enantioselective chromatography of crude reactions provides the stereochemical outcome of asymmetric reactions. The bulk of the data collected offers a clue of the intricate pathways occurring in solution for the studied reactions.
Aminocatalysis; Mass spectrometry; Michael addition; Reaction mechanism; Reaction monitoring
01 Pubblicazione su rivista::01a Articolo in rivista
Primary amine catalyzed activation of carbonyl compounds: a study on reaction pathways and reactive intermediates by mass spectrometry / Iazzetti, A.; Mazzoccanti, G.; Bencivenni, G.; Righi, P.; Calcaterra, A.; Villani, C.; Ciogli, A.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2022:3(2022). [10.1002/ejoc.202101272]
File allegati a questo prodotto
File Dimensione Formato  
Iazzetti_Primary-amin-catalyzed_2021.pdf

accesso aperto

Tipologia: Versione editoriale (versione pubblicata con il layout dell'editore)
Licenza: Creative commons
Dimensione 3.61 MB
Formato Adobe PDF
3.61 MB Adobe PDF Visualizza/Apri PDF

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/11573/1605733
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 1
  • ???jsp.display-item.citation.isi??? 3
social impact