C_2对称性有机小分子催化的高对映选择性Aldol反应  

Highly Enantioselective Aldol Reaction Catalyzed by C_2 Symmetric Organocatalyst

作　　者：顾庆[1] 江玲霞[1] 王琼[1] 伍新燕[1] 

机构地区：[1]华东理工大学教育部结构可控先进功能材料及其制备重点实验室精细化工研究所,上海200237

出　　处：《有机化学》2008年第8期1416-1422,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20402004);上海市自然科学基金(No.06ZR14028)资助项目

摘　　要：以环己酮与4-硝基苯甲醛直接不对称Aldol缩合为模型反应,对一系列具有C2对称性的有机小分子催化剂进行了考察,其中(2S,5S)-吡咯烷-2,5-二羧酸的不对称催化效果最好.在10℃下,以DMSO为溶剂,30%摩尔分数催化剂用量,研究了多个取代芳香醛和环己酮的不对称催化Aldol反应,对映选择性为87%～99%ee.Several C2 symmetric molecules were tested as organocatalysts for the direct catalytic asymmetric aldol reaction of cyclohexanone with 4-nitrobenzaldehyde. （2S,5S）-Pyrrolidine-2,5-dicarboxylic acid afforded the best results for this transformation. The reaction of a series of aromatic aldehydes with cyclohexanone was carried out in DMSO using a catalyst loading of 30 mol% at 10 ℃, and the aldol adducts were obtained in 87%-99% ee.

关 键 词：直接ALDOL反应 不对称催化 有机催化剂 环己酮 

分 类 号：O621.251[理学—有机化学]