The Highly Selective Equatorial Hydride Delivery by Biocatalysis:  Chemoenzymatic Synthesis of trans-2-(4-Propylcyclohexyl)-1,3-propanediol via cis-4-Propylcyclohexanol

4-Propylcyclohexanone 10a (69 g/L) is reduced by the catalysis of Galactomyces geotrichum JCM 6359 using i-PrOH (4.0 equiv) as an auxiliary substrate for recycling externally supplemented NAD+ (0.001 equiv) in 40 mM potassium phosphate buffer (pH 7.5) for 20 h to provide a mixture of cis-4-propylcyc...

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Published inOrganic process research & development Vol. 8; no. 3; pp. 389 - 395
Main Authors Ikunaka, Masaya, Moriya, Narimasa, Nomoto, Fumiki, Ohsako, Akihiro, Okuda, Yoshiaki, Suenaga, Hitoshi
Format Journal Article
LanguageEnglish
Published American Chemical Society 01.05.2004
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Summary:4-Propylcyclohexanone 10a (69 g/L) is reduced by the catalysis of Galactomyces geotrichum JCM 6359 using i-PrOH (4.0 equiv) as an auxiliary substrate for recycling externally supplemented NAD+ (0.001 equiv) in 40 mM potassium phosphate buffer (pH 7.5) for 20 h to provide a mixture of cis-4-propylcyclohexanol 3a [cis/trans (99:0.5); 74%] and unconsumed 10a (22%). Practically pure 3a can be isolated in 69% yield after removing the entailed ketone 10a via bisulfite adduct formation. In the meantime, the crude reduction product [3a/10a (74:22)], without further purification, can be elaborated into trans-2-(4-propylcyclohexyl)-1,3-propanediol 1a, a compound deemed versatile in liquid-crystals development, in 30% overall yield from 10a in four steps.
ISSN:1083-6160
1520-586X
DOI:10.1021/op049961e