%0 Journal Article
%T On the Additions of Lithium Methyl p-Tolyl Sulfoxide to N-(PMP)Arylaldimines
%A Cristina Zucca
%A Pierfrancesco Bravo
%A Eleonora Corradi
%A Stefano V. Meille
%A Alessandro Volonterio
%A Matteo Zanda
%J Molecules
%D 2001
%I MDPI AG
%R 10.3390/60500424
%X 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 (NPMP 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 ˇăC) the additions involving electron-rich N-arylidene groups occur with very high stereocontrol in favor of the (2S,RS)-diastereomers, whereas an electron-deficient group favors the opposite stereochemical outcome. Based on the observations above, a mechanistic hypothesis is proposed.
%K Sulfoxides
%K asymmetric synthesis
%K imines
%U http://www.mdpi.com/1420-3049/6/5/424