On the additions of lithium methyl p-tolyl sulfoxide to N-(PMP)arylaldimines

The results presented in this paper confirm that the stereochemical outcome of the reversible additions of lithium (R)-methyl p-tolyl sulfoxide to N-arylidene-p-anisidines (N-PMP imines) depends on: (a) the reaction conditions used and (b) the electronic properties of the arylidene moiety on the starting imine. In particular, we show that under kinetic control (-70 degreesC) the additions involving electron-rich N-arylidene groups occur with very high stereocontrol in favor of the (2S,R-S)-diastereomers, whereas an electron-deficient group favors the opposite stereochemical outcome. Based on the observations above, a mechanistic hypothesis is proposed.