90862-42-3Relevant academic research and scientific papers
Electro-organic Reactions. Part 22. An Entry into the Quinolizidine and Benzoquinolizidine Ring Systems via Anodic Methoxylation
Palasz, Peter D.,Utley, James H. P.,Hardstone, J. David
, p. 281 - 292 (2007/10/02)
Examples of the quinolizidine and benzoquinolizidine ring systems (1,1-bisethoxycarbonyl-4-oxo-quinolizidine, 1,3,4,6,7,11b-hexahydro-2H-benzoquinolizidine, and 1,2-t-butyl-3,4,6,7,11b-hexahydro-2H-benzo-quinolizidine) have been synthesized by routes which involve initial anodic methoxylation of piperidine precursors with subsequent intramolecular Lewis acid-catalysed cyclisation reactions.Reaction conditions for such cyclisations have been explored; success depends on a correct choice of catalyst (usually aluminium chloride) and, critically, on steric factors.The stereochemistry of the cyclic products has been established and the stereochemical course of the reactions is commented upon.
Electro-organic Reactions. Part 23. Regioselectivity and the Stereochemistry of Anodic Methoxylation of N-Acylpiperidines and N-Acylmorpholines
Palasz, Peter D.,Utley, James H. P.,Hardstone, J. David
, p. 807 - 814 (2007/10/02)
Anodic methoxylation of conformationally biassed N-acylpiperidines has been shown to give axial substitution due to steric constraints imposed by relatively slow rotation of the planar N-acyl groups.These steric constraints also account for the regioselec
