Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 13, Pages 2359-2362Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100150
Keywords
benzaldehyde lyase; benzoin reaction; biocatalysis; borohydrides; ionic liquids
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Funding
- DFG [FOR 1296]
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Stereoselective reduction of 2-hydroxy ketones should in principle give access to syn- and anti-1,2-diols. anti-1,2-Diols are accessible in a highly selective way using zinc borohydride [Zn(BH4)(2)] under chelation control (dr > 20:1). Diastereoselective reduction of unprotected or even protected 2-hydroxy ketones towards syn-1,2-diols could be achieved only with moderate selectivity of dr <= 5:1. Even when using sterically demanding protecting groups and/or polymer-supported borohydride reagents high selectivity could not be achieved. A new ionic liquid-dependent borohydride reduction method, although highly attractive with respect to reaction engineering, resulted in only moderate to good selectivity. An efficient two-step biocatalytic method for the synthesis of syn-1,2-diols is described. The method relies on the whole-cell Pichia glucozyma-catalyzed stereoselective reduction of the unprotected (R)-2-hydroxy ketones (dr > 10: 1). The latter are accessible through thiamine diphosphate-dependent enzyme-catalyzed synthesis starting from simple aldehydes. Thus, biocatalytic transformations enable a process which is hardly accessible through present non-enzymatic methods.
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