Synthesis of Halogenated Carboxylic Acids and Amino Acids

  title={Synthesis of Halogenated Carboxylic Acids and Amino Acids},
  author={Constantin Czekelius and C Christoph Tzschucke},
This review summarizes and focuses on stereoselective methodsfor the preparation of halogenated carboxylic acids and amino acids.Diastereoselective and enantioselective halogen atom transfer processesas well as methods for the synthesis of fluoroalkyl-substitutedcompounds 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… 
45 Citations

Recent advances in the synthesis of fluorinated aminophosphonates and aminophosphonic acids

This review article surveys recent achievements in the preparation and biological properties evaluation of fluorinated aminophosphonates and aminophosphonic acids. Recently, in view of various

Stereoselective access to fluorinated and non-fluorinated quaternary piperidines: synthesis of pipecolic acid and iminosugar derivatives.

The preparation of optically pure quaternary piperidines, both fluorinated and non-fluorinated, has been achieved from a chiral imino lactone derived from (R)-phenylglycinol through the diastereoselective dihydroxylation of suitable synthetic intermediates.

Enantioselective organocatalytic α-heterofunctionalization of active methines

This review aims to illustrate progress in the enantioselective α-amination,α-hydroxylation, α-sulfenylation and α-halogenation reactions of α-substituted 1,3-dicarbonyl and related compounds mediated by mono-, bi-, multi-functional organocatalysts, phosphoric acids and phase transfer catalysts appeared from 2002 to mid-2011.

Structural Elucidation of Enantiopure and Racemic 2-Bromo-3-Methylbutyric Acid

Halogenated carboxylic acids have been important compounds in chemical synthesis and indispensable research tools in biochemical studies for decades. Nevertheless, the number of structurally

Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid

A method specifically developed for large-scale preparation of the target (S)-N-Fmoc-2-amino-4, 4,4,4-trifluorobutanoic acid, which was reproduced several times for consecutive preparation of over 300 g.

Asymmetric Synthesis of 4,4‐(Difluoro)glutamic Acid via Chiral Ni(II)‐Complexes of Dehydroalanine Schiff Bases. Effect of the Chiral Ligands Structure on the Stereochemical Outcome

Abstract Four differently substituted chiral Ni(II)‐complexes of dehydroalanine Schiff base were prepared and reacted with BrCF2COOEt/Cu under the standard reaction conditions. The observed

Trihaloisocyanuric Acids as Atom-Economic Reagents for Halogenation of Aromatics and Carbonyl Compounds in the Solid State by Ball Milling

It is shown that both tribromoisocyanuric acid (TBCA) and trichloroisocyanuric acid (TCCA) are excellent reagents for direct halogenation of electron-rich aromatics under solvent-free, ball-milling

Expedient Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid via Alkylation of Chiral Nucleophilic Glycine Equivalent

Here we disclose a practical asymmetric synthesis of an enantiomerically 97.8% ee pure N-Fmoc derivative of (S)-2-amino-4,4,4-trifluorobutanoic acid performed on >10 g scale of the target product.



Handbook of fluorous chemistry

This chapter discusses the development of strategies for the recovery of Fluorous Catalysts and Reagents in Synthesis and Catalysis, and some of the techniques used to achieve this goal are described.

Synthesis of Halogenated Carboxylic Acids and Amino Acids

  • 2010