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새로운 [3,3]-Sigmatropic Rearrangement를 이용한 입체선택적 아미드의 합성
柳燦模 성균관대학교 기초과학연구소 1993 論文集 Vol.44 No.2
새로운 [3, 3]-sigmatropic rearrangement를 통한 효율적인 입체선택적 amide 합성경로를 개발하였다. 키틴과 3차알릴아민의 부가물의 전위로 97:3의 입체선택적으로 amide가 생성되었다. 이 방법론은 비고리화합물의 입체선택적 합성에 넓은 응용성과 효율성을 나타내었다. A diastereoselective synthetic route to amide through novel [3, 3]-sigmatropic rearrangement has been developed. Rearrangement of adduct between ketene and t-allyamine afforded amide with 97:3 diastereoselection. The method exibited wide applicablity and efficacy for the stereoselective synthesis of acyclic system.
부분입체선택적 Zwitterionic Claisen 전위반응
柳燦模,崔夏洵,李宗昊,鄭元爀 성균관대학교 기초과학연구소 1995 論文集 Vol.46 No.2
Aza-Claisen rearrangement through the zwitterionic intermediate is described. This reaction was able to carry out at low temperature(-78∼0℃) and also exhibited high diastereoselectivities. The formation of zwitterionic intermediate was realized by addition of t-crotylamine to the ketene formed from deprotonation of corresponding acyl halide. The electronically neutral product was achieved through the [3,3]-sigmatropic rearrangement of self-promoted zwitterionic intermediate in high diastereoselectivity due to lower reaction temperature. Treatment of N-crotylpiperidine with propionyl chloride in the presence of K_2CO_3 at 0℃ for 1 h gave threo selective(97 : 3) amide in 41% isolated yield.
수분에 불안정한 2-(Trimethylsilyloxy)furan의 수용체에서의 카르보닐 부가반응 연구
柳燦模,李宗昊,李晟洙,尹淑卿 성균관대학교 기초과학연구소 1995 論文集 Vol.46 No.2
The irreversible addition of 2-(trimethylsilyloxy)furan to various aldehydes in the presence of catalytic amount of alkali metal carbonate in aqueous media is described. Even though alkli metal enolates have many synthetic advantages of applicability and high selections of (E)- and (Z)- enolate geometry, their application to carbonyl addition have been utilized in limited purpose mainly due to the low stereoselectivity resulted from the equilibrium between retroaldol and realdol. The addition of 2-(trimethylsilyloxy)furan to the aldehyde in the presence of K_2CO_3 in aqueous media(THF : H_2O = 9 : 1) at -20℃ resulted in the formation of addition product in high yield and moderate good stereo selection (3-15:1).
김인규,김순일,유찬모,정일국,박준원,심상철,In Kyu Kim,Sun Il Kim,Chan Mo Yu,Il-Gook Chung,Joon Won Park,Sang Chul Shim 대한화학회 1984 대한화학회지 Vol.28 No.6
2-Mercaptobenzothiazole과 알코올로부터 여러가지 알킬유도체를 얻을 수 있었다. 이 방법은 알려진 다른 방법보다 간편하고 수율도 좋고 또 일반성이 있는 장점이 있다. 이렇게 해서 얻은 2-mercaptobenzothiazole에 염소화 반응을 시도한 결과 2-chloromethylthiobenzothiazole을 얻을 수 있었다. A highly efficient and general route to obtain the alkyl derivatives of 2-mercaptobenzothiazole is described. Depending on the reaction conditions 2-methylmercaptobenzothiazole gave various products with chlorinating agents probably due to the lability of the probable chlorosulfonium ion intermediate.