Stereoselective synthesis of (±)-cis-inos-1,3-diamines

Abstract

This contribution presents Stereoselective routes to various cis-inos-1,3-diamines starting from readily available cis-4-aminocyclohexenols (7) and (8). The second nitrogen function is introduced into the ring by use of intramolecular cyclisations of neighbouring trichloroacetimidate groups. Hydrolytic cleavage of the resulting oxazolines (15), (16), (27), (28) and complete deprotection gave new cis-inos-1,3-diamines (31)–(34) in good overall yields.

A further example of Stereoselective introduction of the second nitrogen function is the S_N2-type azide substitution of bromide from O-silylated 1r-amino-3t-bromo-2c,4c-dihydroxycyclohexane (36) and subsequent reduction of the azido function yielding 1r-,3c-diamino-2c,4c-dihydroxycyclohexane (38).