Synlett 2024; 35(02): 165-182
DOI: 10.1055/a-2089-4934
account

Comparison of Diastereoselective ortho-Metalations and C–H ­Activations of Chiral Ferrocenes

Tomáš Čarný
,
This work was supported by the Vedecká Grantová Agentúra (Slovak Grant Agency, VEGA; grant no. VEGA 1/0804/21), and by the Operation Program of Integrated Infrastructure for the project, UpScale of Comenius University Capacities and Competence in Research, Development and Innovation, ITMS2014+: 313021BUZ3, co-financed by the European Regional Development Fund.


Abstract

Chiral ferrocene derivatives possessing a planar stereogenic unit are important as chiral catalysts and materials. The principle method to obtain 1,2-disubstituted planarly chiral ferrocenes is base-mediated ortho-metalation performed on a chiral ferrocene derivative, typically using organolithium bases. A multitude of chiral ligands and other useful compounds have been synthesized by using this methodology. Newer methodologies employing transition-metal-catalyzed C–H bond activation strategies complement ortho-metalation methods and affords access to different types of planar chiral ferrocene derivatives.

1 Introduction

2 Base-Mediated ortho-Deprotonations

3 Diastereoselective C–H Activations

4 Examples of Enantioselective C–H Activations

5 Conclusions



Publication History

Received: 20 April 2023

Accepted after revision: 09 May 2023

Accepted Manuscript online:
09 May 2023

Article published online:
16 June 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany