Polysubstituted 4-piperidones and 4-piperidols: Synthesis and spatial configuration

Triacetonamine was used to synthesize a series of highly substituted 4-piperidones and 4-piperidols. The spatial configuration of these compounds was determined. The anionoid addition to the carbonyl group of these piperidones proceeds through highly stereoselective equatorial attack. The position of the chair-chair-twist conformational equilibrium was determined for the polysubstituted 4-piperidols.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 486–496, February, 1991.