Stereoselective synthesis of 4-hydroxymethyl-1, 3-oxazolidin-2-one derivatives from novel 2-hydroxymethylaziridines. Issue 17 (2nd September 2018)

• Record Type: Journal Article
• Authors: Ouerfelli, Oussema; Tabarki, Mohamed Ali; Pytkowicz, Julien; Arfaoui, Youssef; Brigaud, Thierry; Besbes, Rafâa
• Is Part Of: Synthetic communications. Volume 48:Issue 17(2018)
• Page Start: 2242
• Page End: 2252
• Publication Date: 2018-09-02
• Subjects: 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; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2018.1490771
• Languages: English
• ISSNs: 0039-7911

Abstract

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 SN 1 pathway and a detailed computational study of this mechanistic process has been carried out using theoretical calculations. Graphical Abstract: