Molecules (Apr 2001)

On the Additions of Lithium Methyl p-Tolyl Sulfoxide to N-(PMP)Arylaldimines

  • Matteo Zanda,
  • Alessandro Volonterio,
  • Stefano V. Meille,
  • Eleonora Corradi,
  • Pierfrancesco Bravo,
  • Cristina Zucca

DOI
https://doi.org/10.3390/60500424
Journal volume & issue
Vol. 6, no. 5
pp. 424 – 432

Abstract

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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 °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.

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