The competition between basicity and nucleophilicity of two standard organolithium reagents was studied using DFT. Comparing the reactivity of solvated (MeLi)2 and (LDA)2 toward propanal finally explains why methyllithium adds onto the carbonyl while LDA deprotonates the α-position, in accord with experiment and Ireland's deprotonation TS.
J. Marchois, C. Fressigné, B. Lecachey and J. Maddaluno, Chem. Commun., 2015, 51, 9801 DOI: 10.1039/C5CC01549A
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