ChemInform Abstract: Cyclization of a Chiral N-Crotyl Methoxycarbonylacetamide Mediated by Mn(III). An Easy Entry to (R)-3-Pyrrolidineacetic Acid.
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.