Chiral secondary vic-diamines of diaminobutanediols have been efficiently prepared from L-tartaric acid. Their selective cyclization led to cis-tetraheterodecalines having a (1S,6S)-2, 7-diaza-4,9-dioxa[4.4.0]decane core system. Enantiomerically pure vicinal diamines occur commonly in nature, with many of them having biological properties. Some of them and several synthetic vic-diamines are used as medicinal agents. 1 In the laboratory vic-diamines have found widespread use as chiral ligands in asymmetric reactions, especially C 2 -symmetric vic-diamines with their symmetry element added. 2 Moreover, with the degree of conformational freedom of chiral complexes with a transition metal being reduced in cyclic derivatives, only a few such chiral vic-diamines have been designed. For example bipyrrolidines 1 were used in the asymmetric dihydroxylation of alkenes 3 and the ligand activity of bioxazoles 2, where the two oxazoline rings are directly bonded, has been reported in Cu, Rh, Ir catalyzed asymmetric hydrosilylation of ketones, 4 cyclopropanation of olefins, 5 and transfer hydrogenation of ketones ( Figure 1). 6 Figure 1 Chiral vic-diamines 1-4Several reports show the biological importance of diaminobutanediols. Indeed, drugs based on 1,2,3,4-diaminobutanediols and derivatives showed anticancer properties, and complexes of threo-2,3-diaminobutane-1,4-diol derived from mannitol were used as antitumor agents. 7 These compounds are also the precursors of bioxazoles 3 8 and bioxazolidinones 4, 9 useful for asymmetric hydrosilylation and allylic substitution. 10