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광학활성 B-Alkoxy-9broabicyclo[3.3.1]nonane-Potassium Hydride 환원계에 의한 라세미 에폭시화물의 분할
李光雨,孔亨根,車震淳 嶺南大學校附設 基礎科學硏究所 1986 基礎科學硏究 Vol.6 No.-
In this study, chiral B-alkoxy-9-borabicyclo[3.3.1]nonane-potassium hydride systems were applied to the resolution of representative racemic epoxides, namely 1,2-epoxybutane, 1,2-epoxyoctane and styrene oxide. Chiral B-alkoxy-9-BBN systems were synthesized from the reaction of 9-BBN with (-)-isopinocampheol and (-)-cis-myrtanol, respectively. The resolution of 2 equiv of racemic epoxide was carried out with 1 equiv of the reducing system at 0℃. Thus, the 1 equiv of epoxide was reduced to the alcohol, remaining the other 1 equiv of epoxide intact. The resolving ability of these systems in terms of optical purity of the alcohol appeared to be 25-40% in the case of aliphatic epoxide and 9-12% in the case of styrene oxide. The absolute configuration of the alcohols is consistent with (R)-(-)-aliphatic alcohol and (S)-(-)-1-phenylethanol.