• Bulletin of the Korean Chemical Society
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• 제35권6호
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• pp.1759-1762
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• 2014

The enantioselective ${\alpha}$-chlorination of cyclic ${\beta}$-ketoesters catalyzed by chiral 2-aminoalcohol derivatives (2f) has been developed. For the optically active ${\alpha}$-chlorinated products, the isolated yields are in the range of 85-94% and the enantiomeric excesses are up to 84% ee.

• 청정기술
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• 제17권3호
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• pp.238-243
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• 2011

본 연구에서는 폴리우레탄을 위한 친환경 폴리올 합성을 위하여 피마자유 기반의 폴리올을 합성하였다. 피마자유의 2차 알콜에 다른 촉매 없이 무수말레산을 이용하여 카르복실기를 도입하고, 이를 1차 알콜로 전환하기 위하여 아미노알콜($H_2N$-R-OH) 유도체를 반응시켜 친환경 폴리올을 제조하였다. 다양한 비율의 피마자유와 무수말레산의 반응이 시험 되었으며, 전체 반응은 상대적으로 낮은 공정온도와 무촉매 반응을 기반으로 수행되었다. 긴 곁가지가 도입되어 유동성을 가지고 있는 피마자유 기반의 천연폴리올이 기존의 합성폴리올과 가장 우수한 상용성을 나타내었다.

• 약학회지
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• 제40권3호
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• pp.300-305
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• 1996

The base-induced elimination of N-protected 2-(bromomethyl)pyrrolidines 12a-c with KHMDS in THF at -78$^{\circ}C$ for 1h gave exocyclic enamines 13a-c. The acidic catalyzed pr otonation on ${\beta}$-carbon atom of 2-(methylene)pyrrolidines 13a-c with $H_3PO_4$ formed endocyclic N-iminium intermediates 14(or 15). Nucleophilic attack of alpha-carbon atom and hydrolysis of N-iminium ion gave carbocationic adduct (aminoalcohol) 16 from which 5-amino-2-pentanones 17a-c were formed after deprotonation.

• Bulletin of the Korean Chemical Society
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• 제24권4호
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• pp.460-466
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• 2003

For the drug master file (DMF) of ketoconazole, four impurities (1-4) contained in ketoconazole were synthesized. During the synthesis of 2, a new synthetic method of 1,4-dihydropyrazine was established. To oxidize the aminoalcohol (2j) to the aminal (2j-1), the standard Swern oxidation condition was modified to mask the nucleophilicity of the amino group temporarily using one equivalent of acetic acid. Derivative 3 was synthesized via regioselective bromination at the 2 position of the 4-aminophenol derivative (3a) using $Br_2$ in the presence of p-TsOH. The etherification of aryl bromide with the phenol derivative (1f) was accomplished by a modification of the general Cu-mediated reaction condition using excess 1f itself as a solvent at elevated temperature (190 ℃).