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Synthesis 2007(1): 155-158  
DOI: 10.1055/s-2006-950308
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© Georg Thieme Verlag Stuttgart · New York

Enantiomerically Pure Bis-β-diketones: Valuable Building Blocks for Metallosupramolecular Chemistry

Markus Albrecht*, Sabrina Dehn, Sören Schmid, Marita DeGroot
Institut für Organische Chemie der RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092385; e-Mail: markus.albrecht@oc.rwth-aachen.de;
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Publication History

Received 22 June 2006
Publication Date:
09 October 2006 (online)

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Abstract

A series of enantiomerically pure bis-β-diketone derivatives was prepared by a Claisen-type condensation between protected tartaric acid diesters and several ketones. Hereby the tartaric acid unit is introduced as either a 2,2-dimethyldioxolane or as a 5,6-dimethoxy-5,6-dimethyl-1,4-dioxane derivative. The yields of the Claisen reaction are relatively low, but the starting materials are readily available, so that the one-step procedure leads to the bis-β-diketone derivatives in up to gram quantities.

Key words

Claisen condensation - β-diketone - chirality - ligand

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