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The Stereoisomeric Diaminobutanediol and Dioxadiazadecalin Systems: Synthesis, Structure, Stereoelectronics, and Conformation – Theory vs. Experiment
Author(s) -
Star Alexander,
Goldberg Israel,
Lemcoff N. Gabriel,
Fuchs Benzion
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199909)1999:9<2033::aid-ejoc2033>3.0.co;2-k
Subject(s) - chemistry , diastereomer , stereochemistry , computational chemistry
We present new approaches to the ( C 2 ) 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 ).