Volume 27, Issue 16
Heterocyclic Compounds
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ChemInform Abstract: Cyclization of a Chiral N-Crotyl Methoxycarbonylacetamide Mediated by Mn(III). An Easy Entry to (R)-3-Pyrrolidineacetic Acid.

B. CARDILLO

B. CARDILLO

Dip. Sci. Mater. Terra, Univ. Ancona, I-60131 Ancona, Italy

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R. GALEAZZI

R. GALEAZZI

Dip. Sci. Mater. Terra, Univ. Ancona, I-60131 Ancona, Italy

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G. MOBBILI

G. MOBBILI

Dip. Sci. Mater. Terra, Univ. Ancona, I-60131 Ancona, Italy

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M. ORENA

M. ORENA

Dip. Sci. Mater. Terra, Univ. Ancona, I-60131 Ancona, Italy

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First published: April 16, 1996

Abstract

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ChemInform Abstract

As part of a program aimed at preparing non-proteinogenic amino acids, the synthesis of diastereomerically pure 4-substituted pyrrolidin-2- ones and their conversion to 3-substituted pyrrolidones is studied. Thus, Mn(III)-mediated diastereoselective cyclization of the amide (I) gives an easy separable mixture of the diastereomeric pyrrolidin-2- ones (II) and (III) of which the major isomer (II) is a key intermediate to (R)-3-pyrrolidineacetic acid (VII), an inhibitor of GABA uptake in astrocytes.

chemical structure image

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