Preparation of (S)-2,3-dichloro-1-propanol byPseudomonas sp. and its use in the synthesis of (R)-epichlorohydrin
- 1 February 1992
- journal article
- Published by Oxford University Press (OUP) in Journal of Industrial Microbiology & Biotechnology
- Vol. 9 (2) , 97-101
- https://doi.org/10.1007/bf01569739
Abstract
Pseudomonas sp. OS-K-29 assimilated (R)-2,3-dichloro-1-propanol preferentially as the sole source of carbon. Isolation of optically pure (S)-2,3-dichloro-1-propanol with 100% enantiomer excess (e.e.) from the racemate was done based on this bacterial assimilation using immobilized-cells of OS-K-29 with calcium-alginate. The overall examination of the reactor involved 19 batches for 50 days without loss of its activity. Highly pure (R)-epichlorohydrin with 99.5% e.e. was prepared from the (S)-2,3-dichloro-1-propanol with treatment of aqueous NaOH. This new method is simple and useful for manufacturing optically active (S)-2,3-dichloro-1-propanol and (R)-epichlorohydrin.Keywords
This publication has 16 references indexed in Scilit:
- Lewis acid promoted ring-opening allylation of epichlorohydrin with allylic silanes and stannanes to afford 1-chloro-5-alken-2-ols. A short synthesis of (S)-(-)-ipsenolThe Journal of Organic Chemistry, 1990
- Ferroelectric Liquid Crystals Incorporating the Optically Active γ-Lactone RingJapanese Journal of Applied Physics, 1990
- An efficient synthesis of the optical isomers of nipradilol.CHEMICAL & PHARMACEUTICAL BULLETIN, 1990
- Enantiodivergent Synthesis of Both Enantiomers of Sulcatol and Matsutake Alcohol from (R)-EpichlorohydrinChemistry Letters, 1987
- Preparative production of optically active esters and alcohols using esterase-catalyzed stereospecific transesterification in organic mediaJournal of the American Chemical Society, 1984
- Kinetic resolution of 1,2-diols with D-camphorquinone; preparation of (R)-(chloromethyl)oxiraneJournal of the Chemical Society, Chemical Communications, 1984
- Synthesis of (R,S)-(5Z,8E,10E)-12-hydroxyheptadeca-5,8,10-trienoic acid and of (R,S), and (S)-(5Z,8Z,10E,14Z)-12-hydroxyeicosa-5,8,10,14-tetraenoic acid and their racemic 5,6,8,9-tetradeuterioisomersJournal of the Chemical Society, Perkin Transactions 1, 1982
- Chiral heteroaryloxymethyloxiranesThe Journal of Organic Chemistry, 1979
- Synthesis of (R)- and (S)-epichlorohydrinThe Journal of Organic Chemistry, 1978
- .alpha.-Methoxy-.alpha.-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and aminesThe Journal of Organic Chemistry, 1969