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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 17
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Articles

Stereoselective synthesis of 4-hydroxymethyl-1,3-oxazolidin-2-one derivatives from novel 2-hydroxymethylaziridines

, , , , &
Pages 2242-2252 | Received 03 Mar 2018, Published online: 07 Aug 2018
 

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.

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Supplementary information

Supplemental data of this paper includes full experimental detail and a copy of 1H, 13C NMR. This material can be found via the “Supplementary content” section of the article's webpage.

Additional information

Funding

The authors are grateful to the Tunisian Ministry of Higher Education and Scientific Research for financial support of this research [LR99ES15].

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