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Synthesis 2021; 53(12): 2029-2042
DOI: 10.1055/a-1372-6627
short review

Transient- and Native-Directing-Group-Enabled Enantioselective C–H Functionalization

Bing Zu
a   Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong 518055, P. R. of China
b   School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin, Heilongjiang 150080, P. R. of China
,
Yonghong Guo
a   Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong 518055, P. R. of China
,
Jie Ke
a   Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong 518055, P. R. of China
,
Chuan He  ∗
a   Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong 518055, P. R. of China
› Author AffiliationsWe are grateful for financial support from the Thousand Talents Program for Young Scholars, the Shenzhen Science and Technology Innovation Committee (JCYJ20190809142809370), and the Guangdong Provincial Key Laboratory of Catalysis (2020B121201002).
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Abstract

In recent years, transition-metal-catalyzed enantioselective C–H bond functionalization using chiral transient directing groups (cTDGs) or native directing groups (NDGs) has emerged as a powerful and attractive­ synthetic approach to streamline the synthesis of chiral molecules­. This short review focuses on recent advances on imine-based cTDGs strategies and native amine and carboxylic acid directed strategies for the asymmetric functionalization of various C–H bonds. We have endeavored to highlight the great potential of this methodology and hope that this review will inspire further research in this area.

1 Introduction

2 Transient-Directing-Group-Enabled Enantioselective C–H Functionalization

2.1 Generation of Central Chirality

2.2 Generation of Axial Chirality

2.3 Generation of Planar Chirality

3 Native-Directing-Group-Enabled Enantioselective C–H Functionalization

3.1 Native Amines as Directing Groups

3.2 Native Carboxylic Acids as Directing Groups

4 Conclusions and Outlook

Key words

asymmetric catalysis - enantioselective C–H functionalization - transient directing group - native directing group - synthetic methods


Publication History

Received: 12 December 2020

Accepted after revision: 25 January 2021

Accepted Manuscript online:
25 January 2021

Article published online:
15 February 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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