• KSBB Journal
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• 제26권4호
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• pp.323-327
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• 2011

The convenient derivatization method of chiral amino alcohols as 9-anthraldimine Schiff base derivatives for chiral resolution was developed and the liquid chromatographic enantiomer separation of chiral amino alcohols as 9-anthraldimine derivatives was investigated on several coated and covalently bonded polysaccharide-derived chiral stationary phases (CSPs). In general, the performance of Chiralcel OD-H (or Chiralcel OD) (${\alpha}$ = 1.24-2.89), the coated CSP derived from cellulose derivative was superior to the other CSPs for resolution of 9-anthraldimine derivatives of several amino alcohols. The results of enantioseparation depending on the structure of 9-anthraldimine analytes like the steric bulky group and the polar moiety etc were discussed. The analytical method was applied to measure the enantiomeric purity of commercially available chiral amino alcohols. It is expected that the convenient analytical method will be very efficient for determination of enantiomeric purity of amino alcohols as 9-anthraldimine Schiff base derivatives with strong UV absorption.

• Bulletin of the Korean Chemical Society
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• 제31권4호
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• pp.869-873
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• 2010

A series of novel chiral tert-amino alcohols 4a-h derived from enantiomerically pure phenylalanine were synthesized efficiently and used as chiral ligands in the catalytic enantioselective ethylation of aldehydes with diethylzinc (diethylzinc-to-aldehyde addition). The use of 10 mol % of the amino alcohols led to the corresponding sec-alcohols with excellent enantioselectivities (up to 100% ee) and high yields.

• Bulletin of the Korean Chemical Society
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• 제31권5호
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• pp.1289-1294
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• 2010

Novel $H_8$-binaphthol-based chiral receptors appended with an uryl moiety (2a) and a guanidinium moiety (2b) have been designed and synthesized for the enantioselective recognition of 1,2-amino alcohols via reversible imine formation. The selectivities ($K_R/K_S$ = 9.8 ~ 19.4) of 2b in imine formation with 1,2-amino alcohols are higher than those of 2a ($K_R/K_S$ = 1.8 ~ 4.5). Similar efficiency trend have been observed in the conversion of L-amino acids to D-amino acids, i.e., the efficiency of the receptor 2b (D/L ratio: 4.3 ~ 10.1) is superior to 2a (D/L ratio: 4.0 ~ 8.7).

• Bulletin of the Korean Chemical Society
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• 제30권12호
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• pp.2938-2942
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• 2009

New receptors 1-3 that bind stereoselectively amino alcohols and convert chirality of amino acidsvia imine bond formation were synthesized. The receptors have uryl (1), thiouryl (2) and guanidinium (3) groups all with additional phenylcarbonyl motifs, which are effective hydrogen bonding donors and play a key role in the stereoselective recognitions. The stereoselectivities were measured from the integration of $^1HNMR$ peaks. Compound 1 and 2 showed the stereoselectivities for the imine formation with amino alcohols ($K_R/K_S$) in the range of 2${\sim}$4, and compound 3 in the range of 4${\sim}$8. Chirality conversion efficienciesof 1-3 for amino acids, i.e. D/L ratio at equilibrium, are in the range of 1.5${\sim}$5.6, showing a little higher efficiency with 3. The additional phenylcarbonyl motifs in 1-3 were revealed not to contribute to significant enhancement of the selectivities.

• Bulletin of the Korean Chemical Society
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• 제35권7호
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• pp.1989-1995
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• 2014

The small library of new enantiomerically pure (S,S)-diamino alcohols 1 and their hydroxyldiamide precursors 2 were conveniently synthesized on a gram scale from inexpensive and commercially chiral pool amino acids. The catalytic and induced asymmetric effects of the chiral ligands 1 in the asymmetric allylic oxidation of cycloolefins were investigated.

• Bulletin of the Korean Chemical Society
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• 제24권11호
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• pp.1695-1698
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• 2003

• Bulletin of the Korean Chemical Society
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• 제32권4호
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• pp.1263-1267
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• 2011

Novel binol-based uryl and guanidinium receptors having higher ring conjugation at the periphery of the hydrogen bonding donor sites have been synthesized and utilized to study the enantioselective recognition of 1,2-aminoalcohols and chirality conversion of natural amino acids via imine bond formation. There is a remarkable decrease in the stereoselectivites as the conjugation increases at the periphery of hydrogen bonding donor sites. The guanidinium-based receptors show more selectivity towards the amino alcohol than that of the uryl based ones due to its charge reinforced hydrogen bonds. The conversion efficiency of L-amino acids to Damino acids by the uryl-based receptors is higher than that of the guanidinium-based ones.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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• pp.231.2-232
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• 2002

The synthesis of chiral 1,2-amino alcohols has been an area of intense study in the synthetic and industrial fields, because of their important roles in organic synthesis as fundamental building blocks and their occurrence in a number of natural products. drugs. and chiral auxiliaries or ligands. General methods for the synthesis of these compounds can be divided into two large categories: functional group transformations and the C-C or the C-N bond formations. (omitted)

• 대한화학회지
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• 제33권2호
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• pp.149-155
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• 1989

n-알코올 용매에서 티오아세테이트아미드(TA)의 아미노 양성자의 nmr 화학적 이동과 선모양이 온도를 변화시켜가면서 구하였다. 아미노 양성자의 화학적 이동변화를 용매의 극성 파라미터 중에서 Reichardt의 $E_T(30)$과 연관지어 고찰하였으며, 그들 사이에는 다음의 관계가 있음이 밝혀졌다. ${\delta}_{obs}=a{\cdot}E_T(30)＋b{\cdot}(E_T(30))_2$ 여기서 a는 알코올 용액에서의 용질의 고유한 특성이며, b는 용질-용매 분자간 상호작용의 특성을 나태내고 있다. 또한 선모양 분석에서 얻은 N-C(S) 결합 주위로의 부자유 회전 장애도 아미노 양성자의 화학적 이동의 행동과 유사하게 $E_T(30)$과 밀접한 관계가 있음을 알았다.

• 대한화학회지
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• 제34권6호
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• pp.509-516
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• 1990

n-알코올 용매에서 아세트아미드(AA)의 아미노 양성자의 nmr 화학적 이동과 선모양을 온도의 함수로 조사 연구하였다. 아미노 양성자의 화학적 이동 변화를 용매의 극성 파라미터 중에서 Reichardt의 $E_{T}$(30)으로 고찰하여 그들 사이에 다음과 같은 관계가 존재함을 밝혔다. ${\delta}_{obs}$ = ${\delta}_{o}$ ＋ aE$_{T} (30) ＋ b[E_{T}(30)]^2$ 여기서 ${\delta}_{o}$는 용질의 기체 상태 또는 $E_{T}$(30)가 0인 상태에서의 용질의 화학적 이동이며, a는 알코올 용액에서 용질이 갖는 고유한 특성이며, b는 용질-용매의 상호작용을 나타내는 상수이다. 또한, 선모양의 분석에서 얻은 N-C(O) 결합 주위로의 부자유회전 장애도 아미노 양성자에 대한 화학적 이동의 행동과 유사하게 용매의 $E_{T}$(30)과 밀접한 관계가 있음을 알아 내었다.