Lipshutz Bruce H, Isley Nicholas A, Moser Ralph, Ghorai Subir, Leuser Helena, Taft Benjamin R
Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106, USA.
Adv Synth Catal. 2012 Nov 26;354(17):3175-3179. doi: 10.1002/adsc.201200160.
Using the newly introduced designer surfactant polyethyleneglycol ubiquinol sebacate (PQS), as the platform for micellar catalysis, nonracemic BINAP has been covalently attached and rhodium(I) inserted to form PQS-BINAP-Rh. This species, the first example of a nonracemically-ligated transition metal catalyst-tethered amphiphile, can be utilized for Rh-catalyzed asymmetric conjugate addition reactions of arylboronic acids to acyclic and cyclic enones. These are performed in water at room temperature, while the catalyst can be recycled without its removal from water in the reaction vessel.
利用新引入的设计表面活性剂聚乙二醇癸二酸泛醇酯(PQS)作为胶束催化平台,将非外消旋的联萘酚(BINAP)共价连接并插入铑(I)以形成PQS-BINAP-Rh。该物种是首例非外消旋连接的过渡金属催化剂连接的两亲物,可用于铑催化的芳基硼酸与开链和环状烯酮的不对称共轭加成反应。这些反应在室温下于水中进行,同时催化剂无需从反应容器中的水中除去即可循环使用。