M. Schroeder, J. Kiely, E. Laborde
Oct 1, 1992
Citations
0
Influential Citations
13
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
The use of S-α-methylbenzyl as a chiral auxiliary at N1 allowed separation of diastereomeric 2-pyrrolidinones substituted with an ester, ketoester, ketone and oxime at the C4 position. Reduction of each diastereomer of 4-[1-(hydroxyimino)ethyl]-1-(1-phenylethyl)-2-pyrrolidinone, 10s and 10r, provided a pair of epimeric amines, [11sr and 11ss] and [11rs and 11rr], that were separated by chromatography. The four stereoisomers of 4-(1-aminoethyl)-1-(1-phenylethyl)-2-pyrrolidinone, 11, were elaborated into several stereochemically pure 3-(1-aminoethyl)pyrrolidines, 1 and 15-23. These compounds are useful intermediates (C7 side chains) for quinolone antibacterials.