Efficient synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide

Félix Busqué, Pedro De March, Marta Figueredo, Josep Font, Timothy Gallagher, Sergio Milán

Research output: Contribution to journalArticleResearchpeer-review

42 Citations (Scopus)

Abstract

A convenient synthesis of the title nitrone is reported. The sequence starts from ethyl L-pyroglutamate as the source of chirality and the key step is the generation of an unstable α-methoxy-N-carboxylate ion, which readily decomposes to an imine. The oxidation of the imine with methyl(trifluoromethyl)dioxirane provides the enantiopure nitrone, which is trapped with dimethyl acetylenedicarboxylate. © 2002 Elsevier Science Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)437-445
JournalTetrahedron Asymmetry
Volume13
Issue number4
DOIs
Publication statusPublished - 22 Mar 2002

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