Synthesis of α‐Amino Acids through Samarium(II) Iodide Promoted Reductive Coupling of Nitrones with CO<sub>2</sub>

Prikhod'ko, Alexander I.; Walter, Olaf; Zevaco, Thomas A.; García-Rodríguez, Jaime; Mouhtady, Omar; Py, Sandrine

doi:10.1002/ejoc.201200440

Cited by 13 publications

(7 citation statements)

References 61 publications

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“…Recently,t he use of CO 2 as aC 1 source to access a-AAs has attracted increasing attention. [21] Studies by Prikhodko, Walter, Py et al, [22] as well as Radosevich and co-workers [23] and Mita and Sato, [24] focused on the use of (super)stoichiometric metal reductants (SmI 2 ,M g, or Mn) to generate aamino radicals that can react with CO 2 to access a-AAs.A similar strategy was reported by the groups of Yu [25] and Walsh, [26] through the use of PRC.I nt his case,t he key aamino radicals,g enerated after single-electron reduction of imines,a re further reduced to the corresponding carbanion, which is subsequently trapped by CO 2 to yield a-AAs (Scheme 8A).…”

Section: Co 2 As Ac 1 Building Blockmentioning

confidence: 99%

Radical‐Based Synthesis and Modification of Amino Acids

et al. 2020

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AdriµnG ómez-Suµrez graduated from the University of Santiago de Compostela in 2009. In 2014 he was awarded his PhD from the University of St. Andrews for his studies on the chemistry of dinuclear gold complexes under the supervision of Prof. Steven P. Nolan. Forp ostdoctoral research he moved to the WWU Münster to work with Prof. Frank Glorius. In 2018 he started his habilitation at the Bergische Universität Wuppertal, under the mentorship of Prof. Stefan F. Kirsch. His research interests include radical chemistry,c atalysis, and photochemistry. Scheme 1. Syntheses of a,b-diamino esters. Scheme 2. Synthesis of C-glyco-a-AAs.

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Section: Co 2 As Ac 1 Building Blockmentioning

confidence: 99%

Radical‐Based Synthesis and Modification of Amino Acids

et al. 2020

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“…In 2012, Prikhod'ko, Walter,P y, and co-workersr eported that nitrones werea menable to ar eductivec oupling reactionw ith CO 2 in the presence of an excesso fS mI 2 (7.5 equiv; Scheme 8). [8] They found that 50 atm pressure of CO 2 was necessary to suppress the formation of the undesired dimerization product and to obtain the a-aminoa cids in high yields. Fur-Scheme5.Carboxylation reaction promoted by KOtBu and 18-crown-6.…”

Section: Low-valent-metal-promoted Reductive Coupling Reactionsmentioning

confidence: 99%

Syntheses of α‐Amino Acids by Using CO₂ as a C1 Source

Mita

Sato

2019

Chemistry An Asian Journal

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The incorporation of CO2 into organic compounds is currently one of the most active research topics in organic chemistry, because CO2 is an abundant, inexpensive, nontoxic, and renewable C1 source. However, CO2 is also a thermodynamically stable and kinetically inert gaseous compound, and as such, special strategies are required to activate CO2 and incorporate it into organic compounds. In particular, because the carbon atom adjacent to the nitrogen atom of amine derivatives is positively charged, umpolung carboxylation, which is a difficult chemical process, should be considered for the production of α‐amino acids by using CO2. In this Minireview, we summarize recent synthetic methods for α‐amino acids that use CO2 as a carboxylic acid unit.

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“…In jüngster Zeit hat die Verwendung von CO 2 als C 1 ‐Quelle für den Zugang zu α‐AS zunehmend an Aufmerksamkeit gewonnen [21] . Studien von Prikhod'ko, Walter und Py [22] sowie Radosevich [23] und Mita und Sato [24] konzentrierten sich auf die Verwendung von (über)stöchiometrischen Metall‐Reduktionsmitteln (SmI 2 , Mg oder Mn) zur Erzeugung von α‐Aminoradikalen. Durch Reaktion mit CO 2 sind so α‐AS zugänglich.…”

Section: Introductionunclassified