多手性中心联萘-2-芳甲羟基-2'-醇(Ar-BINMOLs):一类可应用于不对称催化反应的新型手性配体  

1,1'-Binaphthalene-2-α-arylmethanol-2'-ols(Ar-BINMOLs) with Axial and sp^3-Central Chirality: A Novel Chiral Ligands for Catalytic Asymmetric Transformations

作　　者：郑龙生[1] 宋涛[1] 徐利文[1,2] 

机构地区：[1]杭州师范大学有机硅化学及材料技术教育部重点实验室,杭州311121 [2]中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室,兰州730000

出　　处：《有机化学》2014年第7期1255-1267,共13页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21173064);浙江省自然科学基金(No.LR14B03001)资助项目~~

摘　　要：近年来,我们基于1,1'-联萘基-2,2'-二酚(BINOL)为手性源成功地发展了一类多手性中心化合物联萘-2-芳甲羟基-2'-醇(Ar-BINMOLs),它是BINOL的单苄醚化合物经过不对称[1,2]-Wittig重排合成得到的,涉及C—O键的断裂与新C—C的构建反应,由轴手性诱导产生新的碳手性中心,结构独特新颖,同时具有C2轴手性和sp3碳手性的光学纯醇酚类化合物.目前,Ar-BINMOLs作为新型手性配体应用于不对称催化反应已有不少的报道.基于BINOL衍生物以及近几年Ar-BINMOLs及其衍生物的研究进展,重点阐述了其作为新型手性配体或手性骨架在不对称催化反应中的应用研究进展.1-（2-Hydroxynathalen-l-yl）naphthalene-2-ol （BINOL） and its derivatives have been used widely as chiral ligands in asymmetric catalysis. Recently, we have found that the simple axial chiral monoalkylated BINOLs could be converted into synthetically useful and enantiomerically pure 1,1＇-binaphthalene-2-a-arylmethanol-2＇-ols （Ar-BINMOLs） with axial and sp3-eentral chirality through the axial-to-central chirality transfer of [1,2]-Wittig rearrangement. At present, the catalytic ap- plication of Ar-BINMOLs in asymmetric catalysis has been revealed by our and Yus＇s groups. In this account, the progress in the field of B1NOL and its derivatives will also be reported concisely in the article, and the Ar-BINMOLs and its derivatives as new chiral ligands for application in asymmetric catalysis would be summarized detailedly.

关 键 词：手性配体 BINOL 联萘-2-芳甲羟基-2’-醇(Ar—BINMOLs) [1 2]-Wittig重排反应 不对称催化 

分 类 号：O621.251[理学—有机化学]