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Synlett 1992; 1992(10): 837-839
DOI: 10.1055/s-1992-21511
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Asymmetric Nucleophilic Acylation with Metalated Chiral Amino Nitriles: Enantioselective Synthesis of 1,4-Diketones via Asymmetric Michael Addition

Dieter Enders* , Dietrich Mannes, Gerhard Raabe
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-5100 Aachen, Germany
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Publication Date:
08 March 2002 (online)

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Conjugate addition of lithiated chiral α-amino nitriles 4 to cyclohexenone 2 afforded 1,4-diketones 6 in good overall yields and with high enantiomeric excesses. The absolute configuration was confirmed by X-ray structure analysis of the Michael-adduct 5b.