• Title/Summary/Keyword: amino alcohols

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Chiral β-Amino Thiol Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes

  • 강자효;김정환;이준원;김동수;김주인
    • Bulletin of the Korean Chemical Society
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    • v.17 no.12
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    • pp.1135-1142
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    • 1996
  • Reaction of diethylzinc with α-branched aldehydes in the presence of a catalytic amount (5 mol %) of various β-amino thiols in toluene or ether provided the corresponding secondary alcohols in outstanding ee. Detailed preparative procedure for the β-amino thiols are presented.

Interaction of flavins and some alcohols on the molecular level

  • Yu, Byung-Sul;Chung, Hyun-Ho;Lee, Sang-Jong;Kim, Yang-Bae;Kim, Chong-Kook
    • Archives of Pharmacal Research
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    • v.4 no.1
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    • pp.43-51
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    • 1981
  • The effect of some alcohols on the riboflavin derivatives in non-polar solvent was studied by various spectroscopic method in order to support the view point that alcohol may directly interect with the isoalloxazine moiety of FAD, the coenzyme of D-amino-acid oxidase. The most possible association complex between alcohol and riboflavin is the 1:1 complex through the 2-C carbonyl function of the isollaxazine ring nd the hydroxyl proton of alcohol. It is appeared that methanol has a larger association constant than any other alcohols, and the association constant decreases with the carbon number increases and being bulkier in the alkyl group of alcohols.

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Direct Organocatalytic Regioselective α-Hydroxyamination of α-Branched Aldehydes

  • Kim, Sung-Gon;Ahn, Eun-Ju;Park, Tae-Ho
    • Bulletin of the Korean Chemical Society
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    • v.28 no.10
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    • pp.1665-1669
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    • 2007
  • A direct regioselective α-hydroxyamination of α-branched aldehydes with nitrosobenzene using cis-5-benzylproline as catalyst has been developed for the preparation of α-hydroxyamino aldehydes possessing a quaternary carbon center. Such compounds are versatile building blocks for the synthesis of quaternary α- amino acids, β-amino alcohols, and 1,2-diamines.

Enantioselective Synthesis of Cyclic Amino Alcohols: cis-1-Amino-2-indanol

  • Kim, Eun-Jin;An, Kyung-Mi;Ko, Soo Y.
    • Bulletin of the Korean Chemical Society
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    • v.27 no.12
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    • pp.2019-2022
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    • 2006
  • (1S,2R)-cis-1-Amino-2-indanol has been synthesized. A unique feature of the synthesis involves securing the functionalities and the configurations of the two stereocenters on an acyclic precursor before cyclizing it into the final ring-skeleton. The strategy allows both the stereocenters to be controlled in an absolute manner.

Effect of acid or base additive in the mobile phase on enantiomer separation of amino alcohols using polysaccharide derived chiral columns (다당유도체를 기초로 한 키랄 컬럼에서 이동상에서의 산 또는 염기 첨가제가 아미노 알코올의 광학분리에 미치는 영향)

  • Huang, Hu;Jin, Jing Yu;Lee, Wonjae
    • Analytical Science and Technology
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    • v.22 no.4
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    • pp.313-318
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    • 2009
  • Liquid chromatographic enantiomer separation of amino alcohols was performed on several chiral columns based on polysaccharide derivatives under the mobile phase conditions containing acid or base additive. The chromatographic parameters were greatly influenced by the nature of the mobile phase containing acid or base additive as well as the used chiral columns. Compared to chromatographic results obtained in the mobile phase containing base additive (0.1% triethylamine), especially, Chiralcel OD showed dramatically enhanced separation factors and resolution factors with reduced capacity factors under the mobile phase condition containing acidic additive (0.1% trifluoroacetic acid). When the mobile phase containing 0.05% trifluoroacetic acid and 0.05% triethylamine was used on Chiralcel OD, the greatest separation factors and resolution factors among all other mobile phase conditions in this study were observed.

Lithium Aluminum Hydride Reduction Studies of Rigid $\alpha$-Oximino Ketones

  • Kim, Jack C.;Lee, Young-Tae;Kim, Min-Sook;Woo, Young-Min;Shin, Hong-Dae;Cho, In-Seop
    • Bulletin of the Korean Chemical Society
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    • v.3 no.3
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    • pp.119-122
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    • 1982
  • Rigid ${\alpha}$-oximino ketones containing two functional groups such as 2-oximino-1-acenaphthenone and 2-oximino-1-indanone were synthesized and the simultaneous reduction of the two functional groups of ${\alpha}$-oximino ketones by $LiAlH_4$ gave the corresponding amino alcohols, 2-amino-1-acenaphthenol and 2-amino-1-indanol. The yields of the reduction products of the ${\alpha}$ -oximino ketones remarkably increased, as the increase of molar ratio of hydride used to the reactant. The use of 24 moles of $LiAlH_4$ was found to afford the best result in the reduction of the rigid ${\alpha}$-oximino ketones to the corresponding amino alcohols. The yields was not affected by the variation of solvents such as ether, THF and diglyme.

Chiral Molecular Recognition by Alkoxy-amine-aluminum Derivatives (Alkoxy-amine-aluminum 유도체에 의한 키랄 분자 인식)

  • Kim, Jong-Mi
    • Journal of the Korean Society of Industry Convergence
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    • v.12 no.3
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    • pp.143-147
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    • 2009
  • The enantioselective reduction of representative prochiral alkyl-aryl ketones with a new chiral alkoxy-amine-aluminum derivatives from aluminum hydride and ${\alpha},{\alpha}$-diphenyl-${\beta}$-amino alcohols, such as (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol(AMDPB) and (S)-(-)-2-(diphenylhydroxy-methyl)pyrrolidine(DPHMP), in THF at $0^{\circ}C$ was studied. In the reduction of alkoxy-amine-aluminum derivatives, acetophenone, propiophenone, isopropiophenone, and butyrophenone are reduced to corresponding aromatic secoundary alcohols with 34~60 % enantiomeric excess of (S)-isomers. For such ketones, the optical induction was enhanced by increasing a size of alkyl groups.

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Diastereoselective Synthesis of Unsaturated 1,4-Amino Alcohols as a Biologically Important Moiety

  • Jung Young Hoon;Kim Ji Duck
    • 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.