Citation
E. Butkus et al., Enantiomer separation and absolute configuration of densely functionalized2-oxatricyclo[4.3.1.0(3,8)]decanes by CD spectroscopy and chemical correlation, TETRAHEDR-A, 11(15), 2000, pp. 3053-3057
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166
→ ACNP
Volume
11
Issue
15
Year of publication
2000
Pages
3053 - 3057
Database
ISI
SICI code
0957-4166(20000811)11:15<3053:ESAACO>2.0.ZU;2-7
Abstract
Enantiomer separation by HPLC on a swollen microcrystalline triacetylcellul
ose column of highly substituted 2-oxatricyclo[4.3.1.0(3,8)]decane (2-oxapr
otoadamantane) structures afforded enantiomers of this molecule. Applicatio
n of the octant rule to the carbonyl chromophore to establish the absolute
configuration of the enantiomers did not lead to an unequivocal conclusion.
The enantioselective synthesis of 4-bromo-3-methoxy-oxaprotoadamantanone w
as performed from homochiral (+)-(1S,5S)-bicyclo[3.3.1]nonane-2,6-dione thu
s permitting the assignment of the (1R,3S,4S,6R,8R)-configuration to the ti
tle structures. (C) 2000 Elsevier Science Ltd. All rights reserved.