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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%.
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author
; ; and
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
Georg Thieme Verlag
external identifiers
  • wos:000264245600025
  • scopus:63449137477
ISSN
0039-7881
DOI
10.1055/s-0028-1083364
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
a6d602ae-4ed9-49be-9173-8e33c7c7c94f (old id 1402469)
date added to LUP
2016-04-01 13:59:12
date last changed
2025-04-04 15:04:49
@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}},
  keywords     = {{synthesis; kinetic resolution; bicyclic compounds; ketones; chirality}},
  language     = {{eng}},
  number       = {{5}},
  pages        = {{864--867}},
  publisher    = {{Georg Thieme Verlag}},
  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}},
  doi          = {{10.1055/s-0028-1083364}},
  year         = {{2009}},
}