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A Unique (3+2) Annulation Reaction between Meldrum's Acid and Nitrones: Mechanistic Insight by ESI-IMS-MS and DFT
Nicolas Lespes1, Etienne Pair1, Clisy Maganga1
1Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA, 76000, Rouen, France.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 4, 2018
Abstract:
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.