Highly enantiomerically enriched beta-aminoalkanamides 12 and beta-phenylaminoalkanamides 13 have been prepared by the addition reaction of alpha-lithiated 2-alkyl-2-oxazolines 9-Li, derived from optically active oxazolines 9, to N-cumyl nitrones 2. The relative stereochemistry of alkanamides 5 and 6 has been established by 1D-NOESY experiments carried out on the related pyrimidinones 7, whereas the absolute configuration of alkanamides 12 and 13 has been confirmed by an X-ray analysis.
Asymmetric Synthesis of alpha,beta-Substituted beta-Aminoalkanamides and Stereochemical Determination
CAPRIATI, Vito;DEGENNARO, LEONARDO;LUISI, Renzo;
2007-01-01
Abstract
Highly enantiomerically enriched beta-aminoalkanamides 12 and beta-phenylaminoalkanamides 13 have been prepared by the addition reaction of alpha-lithiated 2-alkyl-2-oxazolines 9-Li, derived from optically active oxazolines 9, to N-cumyl nitrones 2. The relative stereochemistry of alkanamides 5 and 6 has been established by 1D-NOESY experiments carried out on the related pyrimidinones 7, whereas the absolute configuration of alkanamides 12 and 13 has been confirmed by an X-ray analysis.File in questo prodotto:
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