SUZUKI CROSS-COUPLING REACTIONS OF NONRACEMIC VINYLBORONO-α-AMINO ACIDS

2001 ◽  
Vol 31 (2) ◽  
pp. 249-255 ◽  
Author(s):  
Sylvain Collet ◽  
Renée Danion-Bougot ◽  
Daniel Danion
Keyword(s):  
Amino Acids ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Structure Ligation Relationship of Amino Acids for the Amination Cross-Coupling Reactions

2019 ◽  
Vol 84 (5) ◽  
pp. 3004-3010 ◽  
Author(s):  
Gargi Nikhil Vaidya ◽  
Arif Khan ◽  
Hansa Verma ◽  
Sanjeev Kumar ◽  
Dinesh Kumar
Keyword(s):  
Amino Acids ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Relationship Of

Synthetic studies of novel ninhydrin analogs

2001 ◽  
Vol 79 (11) ◽  
pp. 1632-1654 ◽  
Author(s):  
Richard R Hark ◽  
Diane B Hauze ◽  
Olga Petrovskaia ◽  
Madeleine M Joullié
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Latent Fingerprints ◽  
Cross Coupling Reactions ◽  
Essential Tool ◽  
Porous Surfaces ◽  
Synthetic Studies ◽  
Sulfur Containing

Ninhydrin is an essential tool in the analysis of amino acids, peptides, and proteins, and the preferred reagent for the detection of latent fingerprints on porous surfaces. The goal of this investigation was to prepare ninhydrin analogs with enhanced chromogenic and fluorogenic properties. Target compounds included structures with extended conjugation and (or) with the presence of sulfur-containing moieties. We have devised general convergent routes for novel heterocyclic and aryl-substituted ninhydrin analogs for use as reagents for amino acid detection.Key words: ninhydrin analogs, synthesis, ketals, Suzuki cross-coupling reactions, Stille cross-coupling reactions.

scholarly journals Synthesis of C 3-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step

2019 ◽  
Vol 15 ◽  
pp. 371-377 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Saidulu Todeti
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Negishi Coupling ◽  
Peptide Dendrimers ◽  
Cross Coupling Reactions ◽  
Synthetic Strategy ◽  
Symmetric Star ◽  
Key Steps

We demonstrate a new synthetic strategy toward star-shaped C 3-symmetric molecules containing α-amino acid (AAA) derivatives and dipeptides. In this regard, trimerization and Negishi cross-coupling reactions are used as the key steps starting from readily available 4’-iodoacetophenone and L-serine. These C 3-symmetric molecules containing AAA moieties are useful to design new ligands suitable for asymmetric synthesis and peptide dendrimers.

ChemInform Abstract: Suzuki Cross-Coupling Reactions of Nonracemic Vinylborono-α-amino Acids.

ChemInform ◽  
2010 ◽  
Vol 32 (27) ◽  
pp. no-no
Author(s):  
Sylvain Collet ◽  
Renee Danion-Bougot ◽  
Daniel Danion
Keyword(s):  
Amino Acids ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Organoboron Reagents in the Preparation of Functionalized ?-Amino Acids

2007 ◽  
Vol 60 (11) ◽  
pp. 799 ◽  
Author(s):  
Peter F. Kaiser ◽  
Quentin I. Churches ◽  
Craig A. Hutton
Keyword(s):  
Amino Acids ◽  
Cyclic Peptide ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Side Chain ◽  
Coupling Reactions ◽  
The Past ◽  
Cross Coupling Reactions ◽  
Metal Catalyzed ◽  
Unsaturated Amino Acids

Over the past decade, major advances in the preparation and utilization of organoboron reagents have been applied to virtually all areas of organic synthesis. The present review collates recent examples of the use of organoboron reagents in the synthesis of α-amino acids and their derivatives. Aryl- and alkenylboronic acids have been used in the asymmetric synthesis of α-amino acids through conjugate addition to unsaturated amino acids and the Petasis three-component coupling reaction. Additionally, α-amino acid derivatives with organoboron functionality on the side-chain have been prepared and used in metal-catalyzed cross-coupling reactions to prepare cross-linked amino acids and complex cyclic peptide natural products.

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian
Keyword(s):  
Functional Group ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
One Step ◽  
Aryl Tosylates ◽  
Low Sensitivity

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

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