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

Article abstract of DOI:10.1016/S0040-4039(00)76863-8

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.