Alternative synthesis of bridgehead polycyclic 1,2-diamines and 2-aminoalcohols from di- and mono-oximes of some bicyclic diketones: Highly improved synthesis of tricyclo[3.3.1.03,7]nonane-3,7-diamine
Bridgehead polycyclic 1,2-diamines 4a and 4b have been obtained from dioximes 2a and 2b, respectively, by two alternative procedures: a) m-chloroperbenzoic acid oxidative coupling to 3a and 3b, followed by reduction with aluminum amalgam, and b) reductive coupling with aluminum amalgam. Similarly, the related 2-aminoalcohols 9a and 9b have been obtained from the corresponding monooximes 7a and 7b.
Synthesis of Bridgehead Polycyclic 1,2-Diamines and 2-Amino Alcohol Derivatives as Rigid Acetylcholine Analogs
Oxidation of dioxime 2a with NBS gave 3 and 4.A chair-boat conformation has been established for 3 by X-ray diffraction analysis, while 4 seems to exist in a chair-chair conformation on the basis of NMR data. m-Chloroperbenzoic acid oxidation of dioximes