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박선영,김현주,임동열,Park, Seon Yeong,Kim, Hyeon Ju,Im, Dong Yeol Korean Chemical Society 2001 Bulletin of the Korean Chemical Society Vol.22 No.9
The chiral amine auxiliary mediated stereoselective alkylation reactions of glycinamides 1-6 and 15-17 using phase transfer catalyst (PTC) for liquid-solid extraction are described. The secondary N-(diphenylmethylene) glycinamides 1, 2 and 3 give better selectivities and yields than tertiary N-(diphenylmethylene) glycinamides 4, 5 and 6. Alkylation of the glycinamide 1 and 2 using 18-Crown-6 as a PTC in toluene at $-40^{\circ}C$ gives best selectivities and yields. Alkylations of N-(4-chlorophenylmethylene)glycinamides 15, 16 and 17 under same PTC conditions give $\alpha$, $\alpha-disubstituted$ amino acid derivatives 18, 19 and 20 with low diastereoselectivities.
Alkoxy-amine-aluminum 유도체에 의한 키랄 분자 인식
김종미(Jong-Mi Kim) 한국산업융합학회 2009 한국산업융합학회 논문집 Vol.12 No.3
The enantioselective reduction of representative prochiral alkyl-aryl ketones with a new chiral alkoxy-amine-aluminum derivatives from aluminum hydride and α,α-diphenyl-β-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 ℃ 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.
정주은(Ju Eun Jung),김희두(Hee Doo Kim) 大韓藥學會 1997 약학회지 Vol.41 No.6
We have synthesized and evaluated (1S, 2R)-1-0-(ethoxycarbonyl)methyl-2,3-0-isopropylidene-1-phenyl-1,2,3-trihydroxypropane(5a) as a novel chiral auxiliary for optically active alpha-hydroxyesters.