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Enantiospecific synthesis and chiroptical properties of bicyclic enones

Orentas, Edvinas; Bagdziunas, Gintautas; Berg, Ulf LU ; Zilinskas, Albinas and Butkus, Eugenijus (2007) In European Journal of Organic Chemistry p.4251-4256
Abstract
The enantiospecific synthesis of several bicyclic enones starting from enantiomerically pure (+)-(1S,5S)-bicyclo[3.3.1]-nonane-2,6-dione (1) was accomplished. The target enones 7-9 were obtained in high yield and purity by using a catalytic amount of benzeneselenic anhydride. (+)-(1S,5R)-bicy-clo[3.3.1]inonane-2,3,6-trione was obtained from diketone 1 by alpha-hydroxylation involving the use of iodine under basic conditions. The reaction included a ring closure/reopening sequence via oxatricyclo[4.3.1.0(3,8)]decane-10-one. It was shown that the latter triketone exists in enone/enol form.
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
chirality, CD spectroscopy, chromopbores, enones, enantiospecific synthesis
in
European Journal of Organic Chemistry
issue
25
pages
4251 - 4256
publisher
John Wiley & Sons
external identifiers
  • wos:000249391800016
  • scopus:34548341842
ISSN
1434-193X
DOI
10.1002/ejoc.200700241
language
English
LU publication?
yes
id
e6e1584f-b1e4-42af-a98d-1e882fc02317 (old id 688107)
date added to LUP
2007-12-19 10:55:15
date last changed
2017-09-10 03:34:15
@article{e6e1584f-b1e4-42af-a98d-1e882fc02317,
  abstract     = {The enantiospecific synthesis of several bicyclic enones starting from enantiomerically pure (+)-(1S,5S)-bicyclo[3.3.1]-nonane-2,6-dione (1) was accomplished. The target enones 7-9 were obtained in high yield and purity by using a catalytic amount of benzeneselenic anhydride. (+)-(1S,5R)-bicy-clo[3.3.1]inonane-2,3,6-trione was obtained from diketone 1 by alpha-hydroxylation involving the use of iodine under basic conditions. The reaction included a ring closure/reopening sequence via oxatricyclo[4.3.1.0(3,8)]decane-10-one. It was shown that the latter triketone exists in enone/enol form.},
  author       = {Orentas, Edvinas and Bagdziunas, Gintautas and Berg, Ulf and Zilinskas, Albinas and Butkus, Eugenijus},
  issn         = {1434-193X},
  keyword      = {chirality,CD spectroscopy,chromopbores,enones,enantiospecific synthesis},
  language     = {eng},
  number       = {25},
  pages        = {4251--4256},
  publisher    = {John Wiley & Sons},
  series       = {European Journal of Organic Chemistry},
  title        = {Enantiospecific synthesis and chiroptical properties of bicyclic enones},
  url          = {http://dx.doi.org/10.1002/ejoc.200700241},
  year         = {2007},
}