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A Unique (3+2) Annulation Reaction between Meldrum's Acid and Nitrones: Mechanistic Insight by ESI‐IMS‐MS and DFT Studies
Author(s) -
Lespes Nicolas,
Pair Etienne,
Maganga Clisy,
Bretier Marie,
Tognetti Vincent,
Joubert Laurent,
Levacher Vincent,
HubertRoux Marie,
Afonso Carlos,
LoutelierBourhis Corinne,
Brière JeanFrançois
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201705714
Subject(s) - annulation , chemistry , electrospray ionization , reactivity (psychology) , stereoselectivity , protonation , nitrone , mass spectrometry , brønsted–lowry acid–base theory , combinatorial chemistry , stereochemistry , ion , organic chemistry , catalysis , cycloaddition , chromatography , alternative medicine , medicine , pathology
The fragile intermediates of the domino process leading to an isoxazolidin‐5‐one, triggered by unique reactivity between Meldrum's acid and an N ‐benzyl nitrone in the presence of a Brønsted base, were determined thanks to the softness and accuracy of electrospray ionization mass spectrometry coupled to ion mobility spectrometry (ESI‐IMS‐MS). The combined DFT study shed light on the overall organocatalytic sequence that starts with a stepwise (3+2) annulation reaction that is followed by a decarboxylative protonation sequence encompassing a stereoselective pathway issue.