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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

By Carl-Johan Wallentin, Edvinas Orentas, Eugenijus Butkus and Kenneth Wärnmark

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%

Topics: Organic Chemistry, synthesis, kinetic resolution, bicyclic compounds, ketones, chirality
Publisher: 'Georg Thieme Verlag KG'
Year: 2009
DOI identifier: 10.1055/s-0028-1083364
OAI identifier: oai:lup.lub.lu.se:a6d602ae-4ed9-49be-9173-8e33c7c7c94f
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