Development of construction of multi-chiral center by one reaction ising meso trick

叔丁基过苯甲酸在Cu (I)-手性N，N-bidente配合物存在下处理4,5-环氧环己-1-烯，得到(3S,4S,5S)-3-苯甲酰氧基-4-环氧环己-1-en，化学收率54%，ee 84%。该化合物衍生为相应的对硝基苯甲酰衍生物后，通过重结晶可将ee提高到100%。产物环氧化物与水开环，臭氧分解得到无环手性三醇。该方法可用于氧化脂类天然产物的合成。

Treatment of 4,5-epoxycyclohex-1-ene with ter-butylperbenzoic acid in the presence of Cu (I)-chiral N,N-bidente complex gave the (3S,4S,5S)-3-benzoyloxy-4-epoxycyclohexa-1-en in 54% chemical yield and 84% ee. The ee of this compound could be increased up to 100% ee by recrystalization after derivatization to the corresponding p-nitrobenzoyl derivative.ring opening of the product epoxide with H2O followed by ozonolysis afforded the acyclic chiral triol. this method is useful for the synthesis of natural product such as oxylipines.