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

…, P de March, M Figueredo, J Font, T Gallagher…

Index: Busque, Felix; De March, Pedro; Figueredo, Marta; Font, Josep; Gallagher, Timothy; Milan, Sergio Tetrahedron Asymmetry, 2002 , vol. 13, # 4 p. 437 - 445

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Citation Number: 43

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.

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