1,3-Diphenylpropane-1,3-diamines XI [1]. Conversion of a 3-hydroxy-1,3-diphenylpropan-1-one to 1,3-diphenylpropane-1,3-diamines

Article abstract of DOI:10.1007/BF00807256

Highly diastereoselective BH₃/THF syn-reduction of the 3-hydroxy-1,3-diphenylpropan-1-one/BBr₃ complex 3/BBr₃ (cf. Sarko) afforded the meso-diol 4, whereas racemate 5 was obtained by BH₃/THF reduction without complexation. Mesylation, exchange of mesylate by azide, and reduction with SnCl₂/thiophenol led to the diamines 10 and 11 which were also produced by reductive N-N cleavage of the 4,5-dihydropyrazole 13.