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 Chemistry,Catalysis

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