• 한국산업융합학회 논문집
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• 제12권3호
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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.

• Archives of Pharmacal Research
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• 제27권10호
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• pp.1009-1015
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• 2004

Quantitative Structure-Resolution Relationship (QSRR) using the Comparative Molecular Field Analysis (CoMFA) software was applied to predict the chromatographic behaviors of chiral drugs with an amine moiety on the chiral cellobiohydrolase (CBH) columns. As a result of the Quantitative CoMFA-Resolution Relationship study, using the partial least square method, prediction of the behavior of drugs with amine moiety upon chiral separation became possible from their three dimensional molecular structures. When a mixed mobile phase of 10 mM aqueous phosphate buffer (pH 7.0) - isopropanol (95 : 5) was employed, the best Quantitative CoMFA-Resolution Relationship, derived from the study, provided a cross-validated $q^2$ = 0.933, a normal $r^2$ = 0.995, while the best Quantitative CoMFA-Separation Factor Relationship, also derived from the study, yielded a cross-validated $q^2$ = 0.939, a normal $r^2$ = 0.991. When all of these results are considered, this QSRR-CoMFA analysis appears to be a very useful tool for the preliminary prediction on the chromatographic behaviors of drugs with an amine moiety inside chiral CBH columns.

• 대한화장품학회지
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• 제49권2호
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• pp.141-146
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• 2023

라세미 혼합물 (헤미에스테르)의 키랄 순도를 효율적으로 측정하기 위한 방법으로 이작용기 (티오우레아와 3차 아민)를 갖는 키랄 이동제 (3)에 대한 연구이다. 다양한 헤미에스테르와 키랄 이동제 (3)의 결합으로 형성된 부분 입체 이성질체에 의해서 헤미에스테르의 메톡시 양성자의 신호가 분명하게 분리되었다. ¹H NMR에서 헤미에스테르의 거울상 이성질체에 대한 분명한 신호 분리는 헤미에스테르의 카르보닐기와 키랄 이동제 (3)의 이작용기(티오우레아와 3차 아민) 사이의 수소 결합에 기인한다. 본 연구는 키랄 이동제 (3)를 사용하여 헤미에스테르의 키랄 순도를 빠르고 간단하게 결정할 수 있는 방법을 제공한다.

• Bulletin of the Korean Chemical Society
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• 제34권7호
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• pp.1955-1956
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• 2013

• Bulletin of the Korean Chemical Society
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• 제16권12호
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• pp.1138-1139
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• 1995

• KSBB Journal
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• 제29권3호
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• pp.205-209
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• 2014

Chromatographic enantiomer resolution of chiral amines was performed on several covalently immobilized and coated chiral stationary phases (CSPs) based on polysaccharide derivatives under the mobile phase conditions containing base or acid or acid/base additive. The chromatographic parameters including separation factors and capacity factors were greatly influenced by the nature of the mobile phase containing base or acid or salt additive as well as the used CSPs. When 0.05% triethylamine/0.05% trifluoroacetic acid as an additive in the mobile phase was used on all CSPs in this study, the greatest enantiomer resolution was observed except for Chiralpak AD. Also, it was shown that the change of base additive into acid or salt in the mobile phase may directly affect chiral recognition mechanisms between the chiral selectors and analytes occurring during enantiomer separation, resulting in the change of elution orders.

• Bulletin of the Korean Chemical Society
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• 제15권1호
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• pp.53-57
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• 1994

A comparison study on asymmetric borane reduction of ketoxime ethers and N-substituted ketimines possesing C = N double bond mediated by the selected chiral oxazaborolidines (1-6) was investigated. Thus, an aromatic ketoxime O-alkyl ether acetophenone oxime O-methyl ether was reduced to the corresponding amine (1-phenylethylamine 8a) with optical yields, such as 58% ee with 1, 86% ee with 2, 3% ee with 3, 99% ee with 4, 60% ee with 5, and 73% ee with 6. However, the reduction of an aliphatic ketoxime derivative 2-heptanone oxime O-methyl ether provided low optical inductions (7-13% ee). For ketoxime O-trimethylsilyl ethers, the reduction of acetophenone O-trimethylsilyl ether afforded 8a with optical yields which were 90% ee with 1, 40% ee with 2, 2% ee with 3, 62% ee with 4, 5% ee with 5, and 60% ee with 6. The reduction of 2-heptanone O-trimethylsilyl ether also gave the product amine with low optical yields (10-40% ee). In the case of N-substituted ketimines, the reduction of acetophenone N-phenylimine afforded the corresponding amine with 79% ee, 78% ee, 9% ee, 73% ee, 78% ee and 67% ee using 1, 2, 3, 4, 5, and 6, respectively, whereas low optical inductions (5-18% ee) for 2-heptanone N-phenylimine were achieved.

• 한국미생물생명공학회:학술대회논문집
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• 한국미생물생명공학회 2002년도 학술발표대회
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• pp.82-82
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• 2002

• Bulletin of the Korean Chemical Society
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• 제34권11호
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• pp.3185-3186
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• 2013

• 대한약학회:학술대회논문집
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• 대한약학회 2000년도 NEW STRATEGY FOR DRUG DEVELOPMENT IN POST-GENOMIC ERA(대한약학회)
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• pp.250.2-251
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• 2000