Next Article in Journal
Molecular and Crystal Structures of Three Berberine Derivatives
Previous Article in Journal
Synthesis and Characterization of Two New p-tert-Butylcalix[4]-arene Schiff Bases
Article Menu

Export Article

Open AccessArticle
Molecules 2001, 6(5), 424-432;

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 / Revised: 3 April 2001 / Accepted: 4 April 2001 / Published: 30 April 2001
Full-Text   |   PDF [93 KB, uploaded 18 June 2014]   |  


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. View Full-Text
Keywords: Sulfoxides; asymmetric synthesis; imines Sulfoxides; asymmetric synthesis; imines

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top