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带有4-(二丙基氨基)吡啶-3-基侧链的螺旋聚(喹喔啉-2,3-二基)作为用于仲醇动力学拆分的手性可切换亲核催化剂

: Helical Poly(quinoxaline-2,3-diyl)s Bearing 4-(Dipropylamino)pyridin-3-yl Pendants as Chirality-Switchable Nucleophilic Catalysts for the Kinetic Resolution of Secondary Alcohols.

作者信息

Yamamoto Takeshi, Murakami Ryo, Suginome Michinori

机构信息

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.

出版信息

Org Lett. 2021 Nov 19;23(22):8711-8716. doi: 10.1021/acs.orglett.1c03134. Epub 2021 Nov 9.

Abstract

Helically chiral poly(quinoxaline-2,3-diyl)s bearing 4-(dipropylamino)pyridin-3-yl pendants at the 5-position of the quinoxaline ring () exhibited high catalytic activities and moderate to high selectivities (up to = 87) in the acylative kinetic resolution of secondary alcohols. The solvent-dependent helical chirality switching of between pure toluene and a 1:1 mixture of toluene and 1,1,2-trichloroethane enabled the preparation of either compound of a pair of enantiomerically pure alcohols (>99% ee) from a single catalyst.

摘要

在喹喔啉环5位带有4-(二丙基氨基)吡啶-3-基侧基的螺旋手性聚(喹喔啉-2,3-二基)()在仲醇的酰化动力学拆分中表现出高催化活性和中等到高的选择性(高达 = 87)。在纯甲苯与甲苯和1,1,2-三氯乙烷的1:1混合物之间, 存在溶剂依赖性螺旋手性转换,这使得能够从单一催化剂制备一对对映体纯醇中的任意一种化合物(>99% ee)。

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