The Stereoisomeric Diaminobutanediol and Dioxadiazadecalin Systems: Synthesis, Structure, Stereoelectronics, and Conformation – Theory vs. Experiment

✍ Scribed by Alexander Star; Israel Goldberg; N. Gabriel Lemcoff; Benzion Fuchs

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 481 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199909)1999:9<2033::aid-ejoc2033>3.0.co;2-k

✦ Synopsis

We present new approaches to the (C 2 ) chiral and meso 1,4-structural, conformational, and stereoelectronic aspects of these systems were probed experimentally and diamino-2,3-butanediol (1) and 2,3-diamino-1,4-butanediol (2) and derivatives. Reactions of these compounds with computationally and provided excellent insight into their properties and behaviour. Good agreement was observed aldehydes to form the novel 1,5-dioxa-3,7-diazadecalin (DODAD) and 1,5-diaza-3,7-dioxadecalin (DADOD) classes between X-ray, NMR, and calculated results of the N,NЈdibenzyl derivatives of trans-DODAD (14) and trans-of compounds (7, 9, 11-15) are also reported. These reactions are diastereospecific, i.e., erythro (meso) or threo starting DADOD (15). compounds lead to trans or cis products, respectively. The ling, the appropriate starting materials being the positional