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Synfacts 2010(5): 0594-0594
DOI: 10.1055/s-0029-1219752
DOI: 10.1055/s-0029-1219752
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Enantioselective Steglich Esterification for the Resolution of 1,2-Diols
R. Hrdina, C. E. Müller, P. R. Schreiner*
Justus-Liebig-Universität Gießen, Germany
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. April 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201005/lookinside/thumbnails/10.1055-s-0029-1219752-1.jpg)
Significance
Schreiner and co-workers employed their recently developed oligopeptide catalyst 3 in a kinetic resolution of trans-cycloalkane-1,2-diols 1 via an enantiodiscriminating Steglich esterification. This work builds on their previous method of employing anhydrides for the same overall transformation (Angew. Chem. Int. Ed. 2008, 47, 6180). The advantage of the current method, apart from its comparably high enantioselectivity and scope, is the increased operational simplicity, broader availability of carboxylic acids compared to anhydrides, and in some cases, higher reaction rates and selectivities for monoacylation.