Synthesis of α‐Alkynyl‐β,β,β‐trifluoroalanine Derivatives by Sonogashira Cross‐Coupling Reaction

Shchetnikov, Grigorii T.; Zotova, Maria A.; Bruneau, Christian; Dixneuf, Pierre H.; Osipov, Sergey N.

doi:10.1002/ejoc.200901354

Cited by 32 publications

(14 citation statements)

References 23 publications

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“…Osipov's group reported the synthesis of racemic α-ethynyl trifluoroalanine esters 37 by using the addition of sodium acetylide 36 to N-protected imines 35, which were derived from α-trifluoropyruvate (Scheme 6). [30] The best yield (67 %) was obtained from N-Cbz-protected (Cbz = carbobenzyloxy) imine 35b. The protected α-ethynyl trifluoroalanine esters 37 were then subjected to Sonogashira coupling reactions with a range of iodobenzenes to give derivatives 38.…”

Section: Addition To N-aryl and N-acyl Iminesmentioning

confidence: 99%

Synthesis of α‐Ethynyl Glycines

Boļšakova

Jirgensons

2016

Eur J Org Chem

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α-Ethynyl glycine derivatives have a high potential for functionalization by derivatization of the amino acid or acetylene moiety, and, as a result, are important intermediates in the construction of biologically active compounds, including natural products. The main methods for the synthesis of ethynyl glycines and glycinols can be divided into six different transformations: (a) homologations of serinal derivatives, (b) nucleophilic alkynylations of α-imino esters/alcohols or their precur-

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Section: Addition To N-aryl and N-acyl Iminesmentioning

confidence: 99%

Synthesis of α‐Ethynyl Glycines

Boļšakova

Jirgensons

2016

Eur J Org Chem

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“…In addition, the insertion of α-amino phosphonates to peptides has shown enhanced antibacterial, antivirus and anticancer activities [ 88 ]. The Ugi reaction provided the azide moieties 84a or 84b , whereas a reaction between sodium acetylide and imines of general structure 86 afforded the alkyne derivatives [ 89 – 90 ]. A subsequent Click reaction gave the final triazole-mimics ( 88a or 88b ) in good to excellent yields (57–97%).…”

Section: Reviewmentioning

confidence: 99%

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

Koopmanschap¹,

Ruijter²,

Orru³

2014

Beilstein J. Org. Chem.

233

117

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SummaryIn the recent past, the design and synthesis of peptide mimics (peptidomimetics) has received much attention. This because they have shown in many cases enhanced pharmacological properties over their natural peptide analogues. In particular, the incorporation of cyclic constructs into peptides is of high interest as they reduce the flexibility of the peptide enhancing often affinity for a certain receptor. Moreover, these cyclic mimics force the molecule into a well-defined secondary structure. Constraint structural and conformational features are often found in biological active peptides. For the synthesis of cyclic constrained peptidomimetics usually a sequence of multiple reactions has been applied, which makes it difficult to easily introduce structural diversity necessary for fine tuning the biological activity. A promising approach to tackle this problem is the use of multicomponent reactions (MCRs), because they can introduce both structural diversity and molecular complexity in only one step. Among the MCRs, the isocyanide-based multicomponent reactions (IMCRs) are most relevant for the synthesis of peptidomimetics because they provide peptide-like products. However, these IMCRs usually give linear products and in order to obtain cyclic constrained peptidomimetics, the acyclic products have to be cyclized via additional cyclization strategies. This is possible via incorporation of bifunctional substrates into the initial IMCR. Examples of such bifunctional groups are N-protected amino acids, convertible isocyanides or MCR-components that bear an additional alkene, alkyne or azide moiety and can be cyclized via either a deprotection–cyclization strategy, a ring-closing metathesis, a 1,3-dipolar cycloaddition or even via a sequence of multiple multicomponent reactions. The sequential IMCR-cyclization reactions can afford small cyclic peptide mimics (ranging from four- to seven-membered rings), medium-sized cyclic constructs or peptidic macrocycles (>12 membered rings). This review describes the developments since 2002 of IMCRs-cyclization strategies towards a wide variety of small cyclic mimics, medium sized cyclic constructs and macrocyclic peptidomimetics.

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“…Following copper-or rhodium-catalyzed dinitrogen extrusion, the resulting CF 3 -containing carbenoid has been found to be efficient in cyclopropanation, [8] ylide generation, [9] ring expansion [10] as well as X-H [11] insertion. In the course of our ongoing studies on the development of new methods for the selective introduction of CF 3 groups into bioactive compounds by means of appropriate building blocks, [12] including α-CF 3 -diazo compounds, [13] herein we wish to disclose our findings on the direct Rh III -catalyzed functionalization of (hetero)arenes by using methyl 3,3,3-trifluoro-2-diazopropionate (1) as a cross-coupling partner.…”

Section: Introductionmentioning

confidence: 99%

CF₃‐Carbenoid C–H Functionalization of (Hetero)arenes under Chelation‐Controlled Rh^III Catalysis

et al. 2015

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An efficient method for the CF3‐carbenoid C–H functionalization of benzenes and indoles using readily available methyl 3,3,3‐trifluoro‐2‐diazopropionate as a cross‐coupling partner under chelation‐controlled RhIII catalysis has been developed. The reactions proceeded smoothly with high regioselectivity in a few hours and allowed the simultaneous introduction of CF3 and carboxylate functions into the 2‐position of directing‐group‐containing benzenes and indoles.

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Synthesis of α‐Alkynyl‐β,β,β‐trifluoroalanine Derivatives by Sonogashira Cross‐Coupling Reaction

Cited by 32 publications

References 23 publications

Synthesis of α‐Ethynyl Glycines

Synthesis of α‐Ethynyl Glycines

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

CF₃‐Carbenoid C–H Functionalization of (Hetero)arenes under Chelation‐Controlled Rh^III Catalysis

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Synthesis of α‐Alkynyl‐β,β,β‐trifluoroalanine Derivatives by Sonogashira Cross‐Coupling Reaction

Cited by 32 publications

References 23 publications

Synthesis of α‐Ethynyl Glycines

Synthesis of α‐Ethynyl Glycines

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

CF3‐Carbenoid C–H Functionalization of (Hetero)arenes under Chelation‐Controlled RhIII Catalysis

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CF₃‐Carbenoid C–H Functionalization of (Hetero)arenes under Chelation‐Controlled Rh^III Catalysis