New supramolecular host systems, 11 - The stereoisomeric diaminobutanedioland dioxadiazadecalin systems: Synthesis, structure, stereoelectronics, and conformation - Theory vs. experiment

We present new approaches to the (C-2) chiral and meso 1,4-diamino-2,3-buta nediol (1) and 2,3-diamino- 1,8-butanediol (2) and: derivatives. Reactions of these compounds with aldehydes to form the novel 1,5-dioxa-3,7-diazadeca lin (DODAD) and 1,5-diaza-3,7-dioxadecalin (DADOD) classes of compounds (7, 9, 11-15) are also reported. These reactions are diastereospecific, i.e., erythro (meso) or threo starting compounds,lead to trans or cis products, r espectively, The structural, conformational, and stereoelectronic aspects o f these systems were probed experimentally and computationally and provided excellent insight into their properties and behaviour. Good agreement was observed between X-ray, NMR, and calculated results of the N,N'-dibenzyl de rivatives of trans-DODAD (14) and trans-DADOD (15).