70384-44-0Relevant academic research and scientific papers
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
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.
