Chiral oligomers by iterative tandem catalysis.

J Am Chem Soc

Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, 5600 MB Eindhoven, The Netherlands.

Published: July 2005

Iterative tandem catalysis is presented as a flexible tool for obtaining chiral macromolecules from racemic or prochiral monomers. Here, we combine lipase-catalyzed ring-opening of omega-substituted lactones with ruthenium-catalyzed racemization. In a two-pot system, enantioenriched oligomers of 6-methyl-epsilon-caprolactone were synthesized, which could not have been obtained by enzymatic ring-opening alone. A one-pot experiment proved highly promising in developing a novel route toward enantiopure polyesters.

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http://dx.doi.org/10.1021/ja052347dDOI Listing

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