Catalytic Asymmetric Construction of CF₃-Substituted Chiral sp³ Carbon Centers

Abstract

Due to the unique steric and electronic nature of the fluorine atom, organofluorine compounds have received significant attention in the fields of pharmaceuticals and agrochemicals. In particular, the CF₃ group is frequently found in biologically active compounds. However, compared to aryl- and alkenyl-CF₃-containing molecules, the construction of sp³ carbon-based alkyl-CF₃-containing molecules, particularly via catalytic enantioselective synthesis, remains a considerable challenge in spite of their high potential in medicinal applications. This short review focuses on recent advances in this research area, and the reported strategies are categorized according to reaction types and starting substrates. In addition, chiral catalysts, substrate scope, and reaction mechanisms are briefly summarized.

1 Introduction

2 Stereoselective Introduction of a CF₃ Group

2.1 Nucleophilic Addition to Carbonyls and Imines

2.2 Electrophilic Substitution at the α Position of Carbonyls

2.3 Allylic Nucleophilic Substitution

3 Stereoselective Functionalization of CF₃-Substituted Molecules

3.1 Electrophilic Substitution of α-CF₃ Carbonyls

3.2 Substitution of α-Halo CF₃ Compounds

3.3 Addition-Type Reactions with CF₃-Substituted Alkenes

4 Conclusion and Outlook

Key words

addition

asymmetric catalysis

fluorine

substitution

trifluoromethyl group

Publikationsverlauf

Eingereicht: 07. April 2022

Angenommen nach Revision: 25. April 2022

Accepted Manuscript online:
25. April 2022

Artikel online veröffentlicht:
09. Juni 2022

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