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On the Additions of Lithium Methyl p-Tolyl Sulfoxide to N-(PMP)Arylaldimines
Dipartimento di Chimica del Politecnico di Milano, via Mancinelli 7, I-20131 Milano, Italy
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; in revised form: 3 April 2001 / Accepted: 4 April 2001 / Published: 30 April 2001
Abstract: 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
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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.
Zucca C, Bravo P, Corradi E, Meille SV, Volonterio A, Zanda M. On the Additions of Lithium Methyl p-Tolyl Sulfoxide to N-(PMP)Arylaldimines. Molecules. 2001; 6(5):424-432.
Zucca, Cristina; Bravo, Pierfrancesco; Corradi, Eleonora; Meille, Stefano V.; Volonterio, Alessandro; Zanda, Matteo. 2001. "On the Additions of Lithium Methyl p-Tolyl Sulfoxide to N-(PMP)Arylaldimines." Molecules 6, no. 5: 424-432.