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Baker's Yeast for Sweet Dough Enables Large-Scale Synthesis of Enantiomerically Pure Bicyclo[3.3.1]nonane-2,6-dione

Wallentin, Carl-Johan LU ; Orentas, Edvinas; Butkus, Eugenijus and Wärnmark, Kenneth LU (2009) In Synthesis p.864-867
Abstract
An improved synthetic procedure of racemic bicyclo[3.3.1]nonane-2,6-dione has been developed. Employing Baker's yeast for sweet dough made it possible to kinetically resolve the racemic compound and to isolate enantiomerically pure (+)-bicyclo[3.3.1]nonane-2,6-dione on a large scale. Furthermore, the developed procedure made it possible to produce (-)-bicyclo[3.3.1]nonane-2,6-dione with an enantiomeric excess of 75%.
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
synthesis, kinetic resolution, bicyclic compounds, ketones, chirality
in
Synthesis
issue
5
pages
864 - 867
publisher
Oxford Polytechnic, Oxford
external identifiers
  • wos:000264245600025
  • scopus:63449137477
ISSN
0039-7881
DOI
10.1055/s-0028-1083364
language
English
LU publication?
yes
id
a6d602ae-4ed9-49be-9173-8e33c7c7c94f (old id 1402469)
date added to LUP
2009-06-15 09:44:16
date last changed
2017-09-10 04:09:20
@article{a6d602ae-4ed9-49be-9173-8e33c7c7c94f,
  abstract     = {An improved synthetic procedure of racemic bicyclo[3.3.1]nonane-2,6-dione has been developed. Employing Baker's yeast for sweet dough made it possible to kinetically resolve the racemic compound and to isolate enantiomerically pure (+)-bicyclo[3.3.1]nonane-2,6-dione on a large scale. Furthermore, the developed procedure made it possible to produce (-)-bicyclo[3.3.1]nonane-2,6-dione with an enantiomeric excess of 75%.},
  author       = {Wallentin, Carl-Johan and Orentas, Edvinas and Butkus, Eugenijus and Wärnmark, Kenneth},
  issn         = {0039-7881},
  keyword      = {synthesis,kinetic resolution,bicyclic compounds,ketones,chirality},
  language     = {eng},
  number       = {5},
  pages        = {864--867},
  publisher    = {Oxford Polytechnic, Oxford},
  series       = {Synthesis},
  title        = {Baker's Yeast for Sweet Dough Enables Large-Scale Synthesis of Enantiomerically Pure Bicyclo[3.3.1]nonane-2,6-dione},
  url          = {http://dx.doi.org/10.1055/s-0028-1083364},
  year         = {2009},
}