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

Alexander Star, Israel Goldberg, N. Gabriel Lemcoff, Benzion Fuchs

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

We present new approaches to the (C2) chiral and meso 1,4-diamino-2,3- butanediol (1) and 2,3-diamino-1,4-butanediol (2) and derivatives. Reactions of these compounds with aldehydes to form the novel 1,5-dioxa-3,7- diazadecalin (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, respectively. The structural, conformational, and stereoelectronic aspects of 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 derivatives of trans-DODAD (14) and trans-DADOD (15).

Original languageEnglish
Pages (from-to)2033-2043
Number of pages11
JournalEuropean Journal of Organic Chemistry
Issue number9
DOIs
StatePublished - 1 Jan 1999
Externally publishedYes

Keywords

  • Conformation analysis
  • Diaminobutanediol
  • Diazadioxadecalin
  • Dioxadiazadecalin
  • Stereoelectronic effects

Fingerprint

Dive into the research topics of 'New supramolecular host systems, 11. The stereoisomeric diaminobutanediol and dioxadiazadecalin systems: Synthesis, structure, stereoelectronics, and conformation - Theory vs. experiment'. Together they form a unique fingerprint.

Cite this