Abstract
The asymmetric synthesis of (R)-2-chloro-1-(m-chlorophenyl)ethanol, a precursor for a key intermediate of an important class of drugs, was achieved by reduction of the corresponding ketone using an acetone powder of Geotrichum candidum with 98% ee and 94% yield based on the starting amount of ketone.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Badone D,Guzzi U (1994) Synthesis of the potent and selective atypical ?-adrenergic agonist SR 59062A. Bioorg. Med. Chem. Lett. 4: 1921-1924.
Bloom JD,Dutia MD,Johnson BD,Wissner A,Burns MG,Largis EE,Dolan JA,Claus TH (1992) Disodium (R,R)-5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]-amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate (CL 316,243). A potent ?-adrenergic agonist virtually specific for beta 3 receptors. A promising antidiabetic and antiobesity agent. J. Med. Chem. 35: 3081-3084.
Itoh N,Mizuguchi N,Mabuchi M (1999) Production of chiral alcohols by enantioselective reduction with NADH-dependent phenylacetaldehyde reductase from Corynebacterium strain, ST-10. J. Mol. Catal. B-Enzym. 6: 41-50.
Kataoka M,Shimizu S,Doi Y,Sakamoto K,Yamada H (1990) Microbial production of chiral pantothenonitrile through stereospecific reduction of 2'-ketopantothenonitrile. Biotechnol. Lett. 12: 357-360.
Matsuda T,Harada T,Nakajima N,Itoh T,Nakamura K (2000) Two classes of enzymes of opposite stereochemistry in an organism: one for fluorinated and another for non-fluorinated substrates. J. Org. Chem. 65: 157-163.
Nakamura K,Matsuda T (1998) Asymmetric reduction of ketones by the acetone powder of Geotrichum candidum. J. Org. Chem. 63: 8957-8964.
Nakamura K,Miyoshi H,Sugiyama T,Hamada H (1995) Diastereo-and enantio-selective reduction of ethyl 2-methyl-3-oxobutanoate by plant cell culture. Phytochemistry 40: 1419-1420.
Randolph TW,Blanch HW,Prausnitz JM,Wilke CR (1985) Enzymatic catalysis in a supercritical fluid. Biotechnol. Lett. 7: 325-328.
Rao AVR,Gurjar MK,Kaiwar V (1992) Enantioselective catalytic reductions of ketones with new four membered oxazaborolidines: application to (S)-tetramisole. Tetrahedron-Asymmetry. 3: 859-862.
Suga T,Hirata T (1990) Biotransformation of exogeneous substrates by plant cell cultures. Phytochemistry 29: 2393-2406.
Takemoto M,Achiwa K,Stoynov N,Chen D,Kutney JP (1996) Synthesis of optically active alpha-phenylpyeidylmethanols by immobilized cell cultures of Cathranthus roseus. Phytochemistry 42: 423-426.
Tanaka K,Yasuda M (1998) A practical synthesis of (R)-3-chlorostyrene oxide starting from 3-chloroethylbenzene. Tetrahedron-Asymmetr. 9: 3275-3282.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Hamada, H., Miura, T., Kumobayashi, H. et al. Asymmetric synthesis of (R)-2-chloro-1-(m-chlorophenyl)ethanol using acetone powder of Geotrichum candidum. Biotechnology Letters 23, 1603–1606 (2001). https://doi.org/10.1023/A:1011922823367
Issue Date:
DOI: https://doi.org/10.1023/A:1011922823367