Orchestration of Concurrent Oxidation and Reduction Cycles for Stereoinversion and Deracemisation of sec-Alcohols
Constance V. Voss, Christian C. Gruber, Kurt Faber, Tanja Knaus, Peter Macheroux and Wolfgang Kroutil*
*Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Email: wolfang.kroutiluni-graz.at
C. V. Voss, C. C. Gruber, K. Faber, T. Knaus, P. Macheroux, W. Kroutil, J. Am. Chem. Soc., 2008, 130, 13969-13972.
DOI: 10.1021/ja804816a (free Supporting Information)
By careful selection of appropriate enzymes (alcohol dehydrogenases [ADH] and cofactor recycling enzymes), cofactor recycling of NADH can be performed in the presence of NADP+ recycling to achieve overall (R)- or (S)-selective deracemisations of sec-alcohols or stereoinversion representing a possible concept for a “green” equivalent to the chemical-intensive Mitsunobu inversion.
see article for more examples
preparative scale (0.4 mmol) - see article for more reactions
proposed reaction pathway for (S)-selective deracemisation