Asymmetric nucleophilic acylation with metalated amino nitriles: Diastereo- and enantio-selective synthesis of 2-substituted 3-aroylcyclohexanones via tandem Michael addition/α-alkylation

Article abstract of DOI:10.1055/s-1995-3968

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.