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Synlett 1991; 1991(11): 797-799
DOI: 10.1055/s-1991-20880
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Asymmetric Electrophilic α-Amidoalkylation, 9:1 Highly Stereoselective Syntheses of 2-Substituted Piperidines

Klaus Th. Wanner* , Elmar Wadenstorfer, Annerose Kärtner
  • *Institut für Pharmazie der Universität München, Sophienstasse 10, D-8000 München, Germany
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Publication Date:
07 March 2002 (online)

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Enantiomerically pure 2-substituted piperidines 8 are synthesized by diastereoselective addition of various nucleophiles 2 to a chiral N-acyliminium ion with an N-acyl group as chiral auxiliary generated in situ from enamide 5 (1-{[(1S,3R)-3-methoxymethyl-2, 2,3- trimethyl-1-triphenylsiloxycyclopentyl]carbonyl}-1,2,3,4-tetrahydropyridine).