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Synlett 2010(7): 991-998  
DOI: 10.1055/s-0029-1219567
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© Georg Thieme Verlag Stuttgart ˙ New York

Deracemisation of Secondary Alcohols via Biocatalytic Stereoinversion

Constance V. Voss, Christian C. Gruber, Wolfgang Kroutil*
Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstr. 28, 8010 Graz, Austria
Fax: +43(316)3809840; e-Mail: wolfgang.kroutil@uni-graz.at;
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Publication History

Received 8 October 2009
Publication Date:
02 March 2010 (online)

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Abstract

The development of various deracemisation concepts from our laboratory for secondary alcohols is summarised. The aim was to find alternatives for dynamic kinetic resolution and related deracemisation concepts. In our improved system, deracemisation is achieved via simultaneous enantioselective oxidation and asymmetric reduction, thereby demonstrating a rare example of concurrent oxidation and reduction in preparative organic chemistry. Such concepts could also be exploited for the racemisation of secondary alcohols through omitting the cofactor recycling.

1 Introduction and Background

2 One Pot, Two Sequential Steps

3 Concurrent Oxidation and Reduction by Compartmentalisation

4 Orchestration of the Oxidation and Reduction

5 Racemisation

6 Conclusion

Key words

deracemisation - secondary alcohols - asymmetric synthesis - biocatalysis - redox reactions

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Geotrichum candidum NBRC 5767, Candida parapsilosis NBRC 0708 (or ATCC 7330), and Sphingomonas paucimobilis NBRC 13934 ( = ATCC 10829, NCIB 8195, NRRL B-54).