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设计并合成含吡咯烷基二茂铁配体及其在手性铑催化烯烃氢化反应中的应用

Design and Synthesis of Pyrrolidinyl Ferrocene-Containing Ligands and Their Application in Highly Enantioselective Rhodium-Catalyzed Olefin Hydrogenation.

机构信息

Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Belfield, D04 N2E5 Dublin, Ireland.

MSD Ballydine, Kilsheelan, Co. Tipperary, E91 V091 Clonmel, Ireland.

出版信息

Molecules. 2022 Sep 17;27(18):6078. doi: 10.3390/molecules27186078.

Abstract

Herein, we report the design and synthesis of a series of chiral pyrrolidine-substituted ferrocene-derived ligands. The proficiency of this novel structural motif was demonstrated in the Rh-catalyzed asymmetric hydrogenation of dehydroamino acid esters and α-aryl enamides. The products were obtained with full conversions and excellent levels of enantioselectivities of up to >99.9% ee and 97.7% ee, respectively, using a BINOL-substituted phosphine-phosphoaramidite ligand which possesses planar, central, and axial chirality elements.

摘要

在此,我们报告了一系列手性吡咯烷取代二茂铁衍生配体的设计和合成。该新型结构基序的效能在脱氢氨基酸酯和α-芳基烯酰胺的 Rh 催化不对称氢化中得到了证明。使用具有平面、中心和轴向手性元素的 BINOL 取代膦-磷酰胺配体,获得了完全转化和高达 >99.9%ee 和 97.7%ee 的优异对映选择性的产物。

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