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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.
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author
; ; ; and
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
Wiley-VCH Verlag
external identifiers
  • wos:000249391800016
  • scopus:34548341842
ISSN
1434-193X
DOI
10.1002/ejoc.200700241
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
id
e6e1584f-b1e4-42af-a98d-1e882fc02317 (old id 688107)
date added to LUP
2016-04-01 11:45:34
date last changed
2025-01-14 17:33:06
@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}},
  keywords     = {{chirality; CD spectroscopy; chromopbores; enones; enantiospecific synthesis}},
  language     = {{eng}},
  number       = {{25}},
  pages        = {{4251--4256}},
  publisher    = {{Wiley-VCH Verlag}},
  series       = {{European Journal of Organic Chemistry}},
  title        = {{Enantiospecific synthesis and chiroptical properties of bicyclic enones}},
  url          = {{http://dx.doi.org/10.1002/ejoc.200700241}},
  doi          = {{10.1002/ejoc.200700241}},
  year         = {{2007}},
}