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Stereoselective synthesis of 4-hydroxymethyl-1,3-oxazolidin-2-one derivatives from novel 2-hydroxymethylaziridines |
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| Authors: | Oussema Ouerfelli Mohamed Ali Tabarki Julien Pytkowicz Youssef Arfaoui Thierry Brigaud |
| Institution: | 1. Faculty of Sciences of Tunis, Laboratory of Analytical Chemistry and Electrochemistry, University of Tunis El Manar, Tunis El Manar, Tunisia;2. Laboratoire de chimie biologique (LCB), Université de Cergy-Pontoise, Cergy-Pontoise cedex, France;3. Laboratoire de chimie biologique (LCB), Université de Cergy-Pontoise, Cergy-Pontoise cedex, France;4. Faculty of Sciences of Tunis, Laboratory of Physical Chemistry of Condensed Matter, University of Tunis El Manar, Tunis El Manar, Tunisia |
| Abstract: | A stereoselective and simple method for the synthesis of trans-2-hydroxymethyl-N-alkyl-1,3-oxazolidin-2-ones is described. The synthesis involved the reduction of trans-aziridine-2-carboxylates with LiAlH4, followed by a ring opening and a cyclization reaction in the presence of methyl chloroformate to afford the target trans-oxazolidinones in completely regio- and stereoselective process. A plausible reaction mechanism has been proposed involving an SN1 pathway and a detailed computational study of this mechanistic process has been carried out using theoretical calculations. |
| Keywords: | Computational study ethyl trans-N-alkylaziridine-2-carboxylates trans-2-hydroxymethyl-N-alkylaziridines trans-2-hydroxymethyl-N-alkyl-1 3-oxazolidin-2-ones ring-expansion reaction |