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Synfacts 2008(8): 0854-0854
DOI: 10.1055/s-2008-1077915
DOI: 10.1055/s-2008-1077915
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Chiral 1,5-Diols by Combined Enzyme and Metal Catalysis
K. Leijondahl, L. Borén, R. Braun, J.-E. Bäckvall*
Stockholm University, Sweden
Further Information
Publication History
Publication Date:
23 July 2008 (online)
![](https://www.thieme-connect.de/media/synfacts/200808/lookinside/thumbnails/10.1055-s-2008-1077915-1.jpg)
Significance
A highly efficient preparation of enantiopure 1,5-diol derivatives is reported. The method combines two known, but very different catalytic processes. On one hand, enzymes convert ‘matched’ epimers of the alcohols into acetates. Concomitantly, a ruthenium catalyst racemizes the ‘unmatched’ alcohols into their ‘matched’ epimers. Therefore, the combination of the reactions permits a 100% theoretical yield of desired chiral product instead of the 50% maximum yield expected for a classic kinetic resolution.