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Synthesis 1995; 1995(6): 659-666
DOI: 10.1055/s-1995-3968
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Asymmetric Nucleophilic Acylation with Metalated Amino Nitriles: Diastereo- and Enantioselective Synthesis of 2-Substituted 3-Aroylcyclohexanones via Tandem Michael Addition/α-Alkylation

Dieter Enders* , Jochen Kirchhoff, Dietrich Mannes, Gerhard Raabe
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany, Fax +49(241)8888127; E-mail Gk010ZO@DACTH11
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Publication Date:
31 December 2000 (online)

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Tandem conjugate addition/α-alkylation of lithiated chiral α-amino nitriles 3 and alkyl bromides to 2-cyclohexenone afforded 2-substituted 3-aroylcyclohexanones 5 of high diastereo- and enantiomeric purity (de ≥98%, ee ≥97-≥99%) and in good overall yields. The absolute configuration of the new stereogenic centres was determined by X-ray structure analysis of the Michael adduct 4c.

asymmetric synthesis - amino nitriles - nucleophilic acylation - Michael addition - 1,4-diketones