Copper‐Catalyzed Asymmetric Arylation of α‐Substituted Cyanoacetates Enabled by Chiral Amide Ligands

Author:

Zhang Rongxing1,Zhou Qinghai2,Wang Xin3,Xu Lanting4,Ma Dawei4ORCID

Affiliation:

1. Chang-Kung Chuang Institute School of Chemistry and Molecular Engineering East China Normal University 500 Dongchuang Lu Shanghai 200062 China

2. The Education Ministry Key Lab of Resource Chemistry Joint International Research Laboratory of Resource Chemistry of Ministry of Education Shanghai Key Laboratory of Rare Earth Functional Materials Shanghai Frontiers Science Center of Biomimetic Catalysis College of Chemistry and Materials Science Shanghai Normal University Shanghai 200234 China

3. Key Laboratory of Structure-Based Drug Design and Discovery Shenyang Pharmaceutical University Ministry of Education Shenyang 110016 China

4. State Key Laboratory of Chemical Biology Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 China

Abstract

AbstractThe (S)‐nobin‐embodied picolinamide and L‐hydroxyproline‐derived amide are effective ligands for Cu‐catalyzed enantioselective coupling reaction of (hetero)aryl iodides with α‐alkyl substituted cyanoacetates. This arylation reaction gave α‐(heteroaryl)‐α‐alkyl cyanoacetates in good to excellent enantioselectivities (up to 95 % ee). A variety of functionalized (hetero)aryl and alkyl groups could be introduced to the quaternary center and therefore provided a valuable tool for preparing enantioenriched compounds with an all‐carbon quaternary center tethered with convertible functional groups. The size of both α‐alkyl and ester groups was proven as the key factor for asymmetric induction.

Funder

Key Technologies Research and Development Program

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Medicine

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3