• Archives of Pharmacal Research
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• v.28 no.4
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• pp.382-390
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• 2005

chial allylic ethers with a hydroxyl group attached to the $\pi-system$ and chlorosulfonyl isocyanate. The enantioselectivity of the CSI reaction with the chiral allylic and benzylic ethers was examined in various solvents and temperatures. Based on these results, it was proposed that the CSI reaction is a competitive reaction of a $S_{N}i$ (retention) and a $S_{N}1$ mechanism (racemization) according to the stability of the carbocation intermediate. This means that there is a greater proportion of retention with the less stable the carbocation intermediate and vise versa.

• Bulletin of the Korean Chemical Society
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• v.16 no.6
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• pp.489-492
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• 1995

A new synthetic route to chiral liquid crystal dopant, 4-[2-(7S-methylnonanyl)oxy-5-pyrimidinyl]phenyl(2S,3S)-2-chloro-3-methylpentanoate (1), starting from 4-nitrophenylacetic acid is described. The key intermediate methylthiopyrimidine compound (8) has been synthesized from 4-nitrophenylacetic acid by Vilsmyer-Haack reaction followed by the formation of pyrimidine ring, and then converted to chiral ester (1) by the replacement of nitro group by (2S,3S)-2-chloro-3-methylpentanoic acid 2 through the formation of diazonium salt.

• Bulletin of the Korean Chemical Society
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• v.12 no.4
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• pp.373-376
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• 1991

Degradation of (-)-laudanosine, a 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloid, with ethyl chloroformate (ECF) afforded an optically active chloro-carbamate as an intermediate. The reason why this intermediate exhibits an optical activity was investigated by comparison with the reactions of some model compounds with ECF. It may be supposed that the chloride group in a hypothetic carbenium ion intermediate stands very closely to the chiral center, so conserving optical activity. However, a neighboring group effect can not be excluded.

• Bulletin of the Korean Chemical Society
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• v.17 no.6
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• pp.493-494
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• 1996

• Archives of Pharmacal Research
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• v.26 no.12
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• pp.997-1001
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• 2003

This paper deals with chiral enzymatic resolution of 4-arylthio-2-butanols by lipase to prepare potential intermediates of $\beta$-lactam antibiotics. Among several lipases employed, lipase P type enzyme gave the highest ee value to prepare (R)-4-arylthio-2-butyl acetate. The enzymatic resolution of phenyl substituted alcohol (6a) using lipase P showed the highest ee value (99.7%) among those of 4-arylthio-2-butanol derivatives. Lipase P mediated hydrolysis of acylester 7a gave also (R)-alcohol 6a selectively. For determination of enantiomeric purity of these enzymatic resolved analytes, liquid chromatographic analysis was performed using two coupled Chiralcel OD and (R,R)-WhelkO chiral column.

• KSBB Journal
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• v.14 no.3
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• pp.291-296
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• 1999

Chiral epoxides are key intermediates for the production of chiral pharmaceuticals, agrochemicals, and functional food additives. Chiral epoxides can be produced by either chemical or biological method. In biocatalytic production routes, chiral epoxides can be produced via epoxidations of prochiral alkenes by monooxygenase or peroxidase. Kinetic resolution of racemic epoxides using whole cells of bacteria or fungi might be commercially useful, since it is possible to obtain chiral epoxides with high optical purities from relatively cheap and readily avaiable racemic epoxides. Some bioprocesses already are commercially developed: the biocatalytic production of chiral epichlorohydrin via microbial stereospecific dehalogenation, and lipase-catalyzed enantioselective hydrolysis in a hollow fiber membrane bioreactor for the production of chiral methyl trans-3-(4-methoxyphenyl)glycidate. the intermediate for calcium antagonist diltiazem. The importance of biocatalytic production of chiral epoxides with several examples from literature are presented.

• Proceedings of the PSK Conference
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• 2001.04a
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• pp.70-71
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• 2001

Naturally occurring azasugar and homologous compounds have been the object of numerous synthetic efforts because these classes of compounds have interesting bioloical activities and the flexibility for the synthesis of chiral alkaloid comounds. As part of a program directed toward the preparation of glycosidase inhibitors, we prepared bicyclic perhydrooxazino- and oxazolopyridine from aminoalcohols and epoxyaldehyde as a common synthetic intermediate.

• Archives of Pharmacal Research
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• v.14 no.2
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• pp.143-146
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• 1991

A new synthetic sequence for the chiral lactone moiety of compactin was developed from $\alpha$-D-glucose in 9 steps via simultaneous reductive detosylation and epoxide-ring opening of 2, 3-epoxy-4-tosylate using NaBH_4$ to afford 2, 4-dideoxy sugar as a key intermediate.

• Bulletin of the Korean Chemical Society
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• v.29 no.2
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• pp.313-318
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• 2008

An enantioselective ring opening of racemic terminal epoxides has been achieved by using heterobimetallic cobalt salen complexes with variety of nucleophiles. They were proven to be highly enantioselective and reactive for the synthesis of valuable chiral building blocks in enantio-riched forms up to 98% ee.

• Bulletin of the Korean Chemical Society
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• v.34 no.5
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• pp.1371-1377
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• 2013

A new synthetic route to N-Cbz-cis-(3R,4R)-3-methylamino-4-methylpiperidine, key intermediate for CP-690,550, was disclosed with L-malic acid as the chiral pool starting material. The title compound was obtained in 16 steps with a total yield of 26% and more than 98% ee.