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Molecules 2001, 6(5), 424-432; doi:10.3390/60500424

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

1, 1,2, 1, 1, 2 and 1,*
1 Dipartimento di Chimica del Politecnico di Milano, via Mancinelli 7, I-20131 Milano, Italy 2 C.N.R. - Centro di Studio sulle Sostanze Organiche Naturali, via Mancinelli 7, I-20131 Milano, Italy
* Author to whom correspondence should be addressed.
Received: 8 March 2001 / Revised: 3 April 2001 / Accepted: 4 April 2001 / Published: 30 April 2001
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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.
Keywords: Sulfoxides; asymmetric synthesis; imines Sulfoxides; asymmetric synthesis; imines
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Zucca, C.; Bravo, P.; Corradi, E.; Meille, S.V.; Volonterio, A.; Zanda, M. On the Additions of Lithium Methyl p-Tolyl Sulfoxide to N-(PMP)Arylaldimines. Molecules 2001, 6, 424-432.

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