A novel dynamic kinetic asymmetric transformation concept employing a ruthenium epimerization catalyst together with an enzyme

ORGN 500

Michaela Edin, Johannes Steinreiber, and Jan-E. Bäckvall. Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory, SE-106 91 Stockholm, Sweden

We have developed a one-step synthesis of enantiomerically pure syn-1,3-diacetates from racemic diastereomeric mixtures of 1,3-diols that relies on: (i) an enzymatic resolution, (ii) a ruthenium-catalyzed epimerization and (iii) an intramolecular acyl migration. The in situ coupling of these three processes results in an efficient enantioselective synthesis of acyclic syn-1,3-diacetates and constitutes a novel concept for dynamic kinetic asymmetric transformation (DYKAT).

 

 

Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, September 8, 2003 Javits Convention Center -- North Pavillion, Sci-Mix

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003