The lithiation and alkylation of aliphatic aldimines has been shown to give syn and anti products in a ratio of 96:4 which is interpreted as representing a minimum value for the syn to anti ratio of the lithiated aldimine intermediates; the factor responsible for the preferential syn stabilization, though not yet identified, is determined to have a magnitude of at least 18 kJ mol–1.
R. R. Fraser and J. Banville, J. Chem. Soc., Chem. Commun., 1979, 47 DOI: 10.1039/C39790000047
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