水相中不同纳米金属促进的羰基化合物和巴豆基溴的丁烯基化反应(英文)  

Crotylation of carbonyl compounds with crotyl bromide mediated by different metal nanoparticles in water

作　　者：周玉青[1] 查正根[1] 徐晓岚[1] 汪志勇[1] 

机构地区：[1]中国科学技术大学化学系,安徽合肥230026

出　　处：《中国科学技术大学学报》2008年第6期647-655,共9页JUSTC

基　　金：NNSFC(20772118;2047078;30572234).

摘　　要：应用纳米铟、铋、锡在水相中成功地促进了多种羰基化合物和巴豆基溴的丁烯基化反应,在短时间内得到了高产率的高烯丙醇.反应的活性、区域选择性、非对映选择性均受不同种类纳米金属的影响.纳米铟促进醛和不活泼的酮与巴豆基溴反应,分别得到了以anti-和syn-异构体为主的γ型产物;纳米铋主要得到以syn-异构体为主的γ型产物;而纳米锡主要得到以anti-异构体为主的γ型产物.同时对反应的机理进行了初步的探讨.Indium, tin and bismuth nanoparticles successfully mediated crotylation of carbonyl compounds in water to afford the corresponding homoallylic alcohols with good to excellent yields in a short time. The reactivity, regioselectivity and diastereoselectivity of crotylation reaction could be adjusted by different metal nanoparticles. The crotylations promoted by indium nanoparticles produced the exclusive γ-adducts with major anti-isomers. Tin nanoparticlemediated crotylation afforded the major γ-adducts with dominant anti-isomers while bismuth nanoparticle-mediated crotylation produced the major γ-adducts with dominant syn-isomers. The proposed mechanism for the crotylation was discussed.

关 键 词：纳米金属促进剂 羰基化合物 丁烯基化 非对映选择性 水 

分 类 号：O621.258[理学—有机化学]