文献类型：期刊文献

英文题名：A Highly Selective Ferrocene-Based Planar Chiral PIP (Fc-PIP) Acyl Transfer Catalyst for the Kinetic Resolution of Alcohols

作者：Hu, Bin[1];Meng, Meng[1];Wang, Zheng[1];Du, Wenting[1];Fossey, John S.[1,2];Hu, Xinquan[3];Deng, Wei-Ping[1]

机构：[1]E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[2]Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England;[3]Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310014, Zhejiang, Peoples R China

年份：2010

卷号：132

期号：47

起止页码：17041

外文期刊名：JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

收录：;EI(收录号：20104813447387);WOS:【SCI-EXPANDED(收录号:WOS:000284972400048)】；

基金：W.-P.D. is thankful for financial support from the New Century Excellent Talents in University, the Ministry of Education, China (NCET-07-0283), the Shanghai Committee of Science and Technology (Grant 06PJ14023), and the "111" Project (B07023). J.S.F. thanks ECUST for a Visiting Professorship, ERDF AWMII, and the University of Birmingham for support. W.-P.D. and J.S.F. thank the CAtalysis and Sensing for our Environment (CASE) network and the CASE09 Workshop at ECUST for networking opportunities.

语种：英文

外文关键词：Catalyst selectivity - Iron compounds - Organometallics

摘要：Novel planar chiral ferrocene nucleophilic catalysts (Fc-PIP) containing both central and planar chiral elements were designed and synthesized for catalytic enantioselective acyl transfer of secondary alcohols. A remarkably efficient catalyst with high selectivity factors (up to S = 1892) was identified. Comparing the combination of central and planar chirality revealed a strong requirement for the "matched" chiral elements, indicating that the stereogenic center of the imidazole rings should present itself on the same face as the ferrocenyl fragment; otherwise, the catalyst is completely inactive. An exclusively stacked transition state that accounts for the high selectivity of the kinetic resolution of secondary alcohols is proposed. Notably, this newly designed catalyst family is suitable for the catalytic kinetic resolution of bulky arylalkyl carbinols, producing esters with extremely high ee (>99%).