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

doi:10.1016/S0957-4166(02)00110-6

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

Department of Chemistry

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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 language	English
Pages (from-to)	437-445
Journal	Tetrahedron Asymmetry
Volume	13
Issue number	4
DOIs	https://doi.org/10.1016/S0957-4166(02)00110-6
Publication status	Published - 22 Mar 2002

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

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. {\textcopyright} 2002 Elsevier Science Ltd. All rights reserved.",

author = "F{\'e}lix Busqu{\'e} and {De March}, Pedro and Marta Figueredo and Josep Font and Timothy Gallagher and Sergio Mil{\'a}n",

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T1 - Efficient synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide

AU - Busqué, Félix

AU - De March, Pedro

AU - Figueredo, Marta

AU - Font, Josep

AU - Gallagher, Timothy

AU - Milán, Sergio

PY - 2002/3/22

Y1 - 2002/3/22

N2 - 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.

AB - 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.

U2 - 10.1016/S0957-4166(02)00110-6

DO - 10.1016/S0957-4166(02)00110-6

M3 - Article

VL - 13

SP - 437

EP - 445

IS - 4

ER -

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

Abstract

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