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 °C) 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.
ASYMMETRIC ADDITIONS OF α-SULFOXIDE CARBANION ON IMINES
The formation of the anion of methyl p-tolyl sulfoxide was studied in various experimental conditions.This allowed to get a very good control of diastereoselectivity during addition of the above carbanion on many imines.Various stereoisomerically pure ami
Ronan, B,Marchalin, S,Samuel, O,Kagan, H. B.
p. 6101 - 6104
(2007/10/02)
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