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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.
김인규,이병석,홍영택,최하순,권남연,Kim, In Gyu,Lee, Byeong Seok,Hong, Yeong Taek,Choe, Ha Sun,Gwon, Nam Yeon 대한화학회 1994 대한화학회지 Vol.38 No.10
Dolastatin 10의 유사체를 합성하기 위한 연구의 일환으로 여러 형태의 펩티드 화합물의 합성 경로를 연구하였다. 유사체의 합성에 사용된 4-amino-3-hydroxy acid는 에폭시 화합물의 아민에 의한 고리열림에 의하여 합성하였다. 이 비단백질 아미노산응로부터 주로 DCC 축합에 의하여 펩티드 화합물을 합성하였다. As a part of synthetic programs aimed at Dolastatin 10 analogues, synthetic pathway toward various peptides were investigated. 4-Amino-3-hydr> Transfer interrupted!nalogues were prepared by ring opening of epoxides with ammonia in MeOH. Several peptides were prepared starting from these unusual amino acids through using mainly DCC coupling.