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用于铑催化的芳基硼酸对甲苯磺酰芳基亚胺的高对映选择性加成反应的基于手性苯骨架的亚砜-烯烃配体

Chiral benzene backbone-based sulfoxide-olefin ligands for highly enantioselective Rh-catalyzed addition of arylboronic acids to -tosylarylimines.

作者信息

Xue Feng, Liu Qibin, Zhu Yong, Qing Yunfei, Wan Boshun

机构信息

Key Laboratory of Functional Organic Molecules of Xinxiang City Henan Province, College of Chemistry and Chemical Engineering, Henan Institute of Science and Technology Xinxiang Henan 453002 China

Dalian Allychem Co., Ltd 5 Jinbin Road Dalian 116620 China

出版信息

RSC Adv. 2019 Aug 14;9(44):25377-25381. doi: 10.1039/c9ra04836g. eCollection 2019 Aug 13.

Abstract

An efficient Rh-catalyzed addition of arylboronic acids to -tosylarylimines has been developed with chiral benzene backbone-based sulfoxide-olefin ligands, where 2-methoxy-1-naphthyl sulfinyl functionalized olefin ligands have shown to be more effective. The versatile method tolerates a wide range of functional groups and shows broad scope without regard to electronic or steric substitution pattern, allowing access to a broad range of chiral diarylmethylamines in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee).

摘要

利用基于手性苯骨架的亚砜-烯烃配体,开发了一种高效的铑催化芳基硼酸与对甲苯磺酰芳基亚胺的加成反应,其中2-甲氧基-1-萘基亚磺酰基官能化的烯烃配体已证明更有效。该通用方法可耐受多种官能团,且不受电子或空间取代模式的影响,适用范围广泛,能够以高收率(高达99%)和优异的对映选择性(高达99% ee)获得多种手性二芳基甲胺。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42a6/9070081/008d79006280/c9ra04836g-s1.jpg

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