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Azomethine ylides from nitrones: Using catalytic nBuLi for the totally stereoselective synthesis of trans-2-alkyl-3-oxazolines

AuthorsJuste-Navarro, Verónica; Delso, J. Ignacio; Tejero, Tomás ; Merino, Pedro
KeywordsDensity functional calculations
Azomethine ylides
Issue Date2016
CitationChemistry - A European Journal 22(33): 11527-11532 (2016)
AbstractThe cycloaddition of azomethine ylide N-oxides (nitrone ylides) with aldehydes provides 3-oxazolines in a completely stereoselective manner in the presence of a catalytic amount of n-butyllithium. The process involves an initial nucleophilic attack on the aldehyde, followed by intramolecular oxygen addition to the nitrone moiety and lithium-assisted elimination of water, regenerating the catalytic species. Various Li-based catalytic systems are possible and the in situ generated water is required for continuing the catalytic cycle. The best results are observed with 20 mol % of n-butyllithium, whereas the use of stoichiometric amounts inhibit the rate of catalysis. Experimental, spectroscopic, and computational mechanistic studies have provided evidence of lithium-ion catalysis and rationalized several competing catalytic pathways.
Identifiersdoi: 10.1002/chem.201602159
e-issn: 1521-3765
issn: 0947-6539
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