Synthesis of ferrocenoyl amino acid derivatives via homogeneous catalytic aminocarbonylation

Kuik, Árpád; Skoda‐Földes, Rita; Balogh, János; Kollár, László

doi:10.1016/j.jorganchem.2005.03.054

Cited by 21 publications

(10 citation statements)

References 34 publications

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“…1 -(3-aminopropyl)ferrocene-1-carboxylic acid, 1 -amino-1-ferrocenebutyric acid) and their derivatives 260 were reported and described by Rapi et al [88] and, recently, syntheses of N-ferrocenylglyoxyl amino acid derivatives 261 were published by Skoda-Földes et al [89] (Fig. 1 -(3-aminopropyl)ferrocene-1-carboxylic acid, 1 -amino-1-ferrocenebutyric acid) and their derivatives 260 were reported and described by Rapi et al [88] and, recently, syntheses of N-ferrocenylglyoxyl amino acid derivatives 261 were published by Skoda-Földes et al [89] (Fig.…”

Section: Ferrocenyl Amino Acidsmentioning

confidence: 99%

Recent Advances in the Synthesis of Unnatural α-Amino Acids

Perdih¹,

Dolenc

2007

COC

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The synthesis of unnatural -amino acids is an area of research that has gained a lot of attention in recent years. The availability of synthetic methods for novel unnatural amino acid derivatives and related compounds will be a critical point in the de novo design of molecules that mimic the conformation of the natural, active peptides. These molecules (peptidomimetics) are designed to display high receptor affinity and selectivity, in addition to enhanced bioavailability and metabolic stability.This review focuses on selected recent synthetic methodologies leading to unnatural -amino acids including chiral catalysts that enable enantioselective synthesis and microwave-assisted synthesis. Solid phase synthesis and construction of organometallic amino acids reveal the scope of influence that this field has in organic chemistry. Additionally, the article is aimed to provide a brief insight into the biosynthetic approaches to the synthesis of -amino acid derivatives, and to give the reader an appreciation of the field.

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Section: Ferrocenyl Amino Acidsmentioning

confidence: 99%

Recent Advances in the Synthesis of Unnatural α-Amino Acids

Perdih¹,

Dolenc

2007

COC

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“…A huge series of amino acid and peptide derivatives of ferrocene‐1,1′‐dicarboxylic acid has been synthesized by coupling amino acid esters and peptide esters with 1,1′‐ferrocene dicarboxylic acid or with ferrocenyl carbonyl chloride. Another route to ferrocenoyl amino acid derivatives is the palladium‐catalyzed aminocarbonylation of iodoferrocene 213. The “ferrocene‐dipeptide bioconjugates” have attracted the interest because of their fascinating highly ordered intramolecular hydrogen‐bridged structure (Scheme , Equation (30)), which was first discovered by Herrick et al214 and which has been extensively and successfully studied by Hirao and Moriuchi ,215 Kraatz ,216 Metzler‐Nolte and Schatzschneider ,217,218 and Heinze and Rapic 219.…”

Section: Peptide Synthesis At Functionalized and π‐Coordinated Armentioning

confidence: 99%

Metal Complexes of Biologically Important Ligands, CLXXVI.[1] Formation of Peptides within the Coordination Sphere of Metal Ions and of Classical and Organometallic Complexes and Some Aspects of Prebiotic Chemistry

Beck

2011

Zeitschrift anorg allge chemie

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“…The reaction was described to proceed with both 1-iodoferrocene and 1,1'-diiodoferrocene with moderate to good yields. A nice entry to ferrocenyl amino acid derivatives (86)-(88) was also described by using protected amino-acids as the amine partners in the reaction [73,74] (Fig. (17)).…”

Section: Ferrocene-co Bond: Aminocarbonylationmentioning

confidence: 99%

Metal-Catalyzed Cross-Coupling Reactions for Ferrocene Functionalization: Recent Applications in Synthesis, Material Science and Asymmetric Catalysis

Mamane¹

2008

MROC

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Recent examples on the functionalization of the ferrocene core by means of cross-coupling reactions are reported in this review. Several methods are discussed including Negishi, Suzuki and Stille couplings for ferrocene-aryl bond formation and Sonogashira reaction for ferrocene-alkyne coupling. The properties in material science and asymmetric catalysis of the prepared ferrocenyl compounds are briefly discussed.

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Synthesis of ferrocenoyl amino acid derivatives via homogeneous catalytic aminocarbonylation

Cited by 21 publications

References 34 publications

Recent Advances in the Synthesis of Unnatural α-Amino Acids

Recent Advances in the Synthesis of Unnatural α-Amino Acids

Metal Complexes of Biologically Important Ligands, CLXXVI.[1] Formation of Peptides within the Coordination Sphere of Metal Ions and of Classical and Organometallic Complexes and Some Aspects of Prebiotic Chemistry

Metal-Catalyzed Cross-Coupling Reactions for Ferrocene Functionalization: Recent Applications in Synthesis, Material Science and Asymmetric Catalysis

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