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DOI: 10.1055/s-0029-1218649
Synthesis of Halogenated Carboxylic Acids and Amino Acids
Publication History
Publication Date:
25 January 2010 (online)
Abstract
This review summarizes and focuses on stereoselective methods for the preparation of halogenated carboxylic acids and amino acids. Diastereoselective and enantioselective halogen atom transfer processes as well as methods for the synthesis of fluoroalkyl-substituted compounds are discussed in detail.
1 Introduction
2 Stereoselective Halogenation Reactions
2.1 Diastereoselective Transformations
2.2 Processes Employing Chiral Auxiliaries
2.3 Organocatalytic Methods
2.4 Chiral Halogenating Reagents
2.5 Halogenations with Chiral Lewis Acids
3 Stereoselective Fluoroalkylation
3.1 Nucleophilic Fluoroalkylations
3.1.1 Trifluoromethylations
3.1.2 Monofluoromethylations and Difluoromethylations
3.1.3 α-Fluoro-β-keto Esters as Nucleophiles
3.1.4 Difluoroacetate-Derived Nucleophiles
3.2 Radical Fluoroalkylations
3.3 Electrophilic Trifluoromethylation
3.4 Reactions of α-Trifluoromethyl-Substitituted Enolates
3.5 Nucleophilic Additions to Trifluoropyruvate
4 Concluding Remarks
Key words
halogens - fluorine - trifluoromethylation - enantioselective methods - organocatalysis
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