Cross-Dehydrogenative Coupling Reactions by Transition-Metal and Aminocatalysis for the Synthesis of Amino Acid Derivatives

Abstract: A natural driving force is always working behind the synthetic organic chemists towards the development of ‘green’ synthetic methodologies for the synthesis of useful classes of organic molecules having potential applications. The majority of the essential classes of organic transformations, including C-C and C-X (X = heteroatom) bond-forming crosscoupling reactions, cross dehydrogenative-coupling (CDC) mostly rely on the requirement of transition-metal catalysts and hazardous organic solvents. Hence, the scope in developing green synthetic strategies by avoiding the use of transitionmetal catalysts and hazardous organic solvents for those important and useful classes of organic transformations is very high. Hence, several attempts are made so far. Water being the most abundant, cheap, and green solvent in the world; numerous synthetic methods have been developed in an aqueous medium. In this review, the development of transitionmetal- free green synthetic strategies for various important classes of organic transformations such as C-C and C-X bondforming cross-coupling, cross dehydrogenative-coupling, and oxidative-coupling in an aqueous media is discussed.

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Synthesis of β-hydroxy-α-amino acid derivatives by the cross-dehydrogenative coupling of N-arylglycine esters with α-hydroxy ketones

Tetrahedron ◽

10.1016/j.tet.2021.132491 ◽

2021 ◽

pp. 132491

Author(s):

JunJiao Wang ◽

Yuyu Lv ◽

Yongwei Shang ◽

Zhoubin Deng ◽

Jianzhong Zhang ◽

...

Keyword(s):

Amino Acid ◽

Amino Acid Derivatives ◽

Dehydrogenative Coupling ◽

Hydroxy Ketones ◽

The Cross

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Cross-Dehydrogenative Coupling Reactions for the Functionalization of α-Amino Acid Derivatives and Peptides

Synthesis ◽

10.1055/s-0037-1610073 ◽

2018 ◽

Vol 50 (15) ◽

pp. 2853-2866 ◽

Cited By ~ 21

Author(s):

Arkaitz Correa ◽

Marcos Segundo

Keyword(s):

Amino Acid ◽

Carbonyl Compounds ◽

Bond Formation ◽

Short Review ◽

Great Promise ◽

Coupling Reactions ◽

Atom Economy ◽

Bond Forming ◽

Dehydrogenative Coupling ◽

Peptide Derivatives

The functionalization of typically unreactive C(sp3)–H bonds holds great promise for reducing the reliance on existing functional groups while improving atom-economy and energy efficiency. As a result, this topic is a matter of genuine concern for scientists in order to achieve greener chemical processes. The site-specific modification of α-amino acid and peptides based upon C(sp3)–H functionalization still represents a great challenge of utmost synthetic importance. This short review summarizes the most recent advances in ‘Cross-Dehydrogenative Couplings’ of α-amino carbonyl compounds and peptide derivatives with a variety of nucleophilic coupling partners.1 Introduction2 C–C Bond-Forming Oxidative Couplings2.1 Reaction with Alkynes2.2 Reaction with Alkenes2.3 Reaction with (Hetero)arenes2.4 Reaction with Alkyl Reagents3 C–Heteroatom Bond-Forming Oxidative Couplings3.1 C–P Bond Formation3.2 C–N Bond Formation3.3 C–O and C–S Bond Formation4 Conclusions

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The Schöllkopf chiron and transition metal mediated reactions, a powerful combination for stereoselective construction of cyclic α-quaternary-α-amino acid derivatives

Amino Acids ◽

10.1007/s00726-007-0512-5 ◽

2007 ◽

Vol 34 (3) ◽

pp. 357-402 ◽

Cited By ~ 29

Author(s):

K. Undheim

Keyword(s):

Amino Acid ◽

Transition Metal ◽

Amino Acid Derivatives

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ChemInform Abstract: Synthesis of Enantiomerically Enriched α-Amino Acid Derivatives via Transition Metal Catalyzed Procedures.

ChemInform ◽

10.1002/chin.199602255 ◽

2010 ◽

Vol 27 (2) ◽

pp. no-no

Author(s):

R. JUMNAH ◽

A. C. WILLIAMS ◽

J. M. J. WILLIAMS

Keyword(s):

Amino Acid ◽

Transition Metal ◽

Amino Acid Derivatives ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

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Equilibrium and structural studies on transition metal complexes of amino acid derivatives containing the bis(pyridin-2-yl)methyl residue

New Journal of Chemistry ◽

10.1039/b010212l ◽

2001 ◽

Vol 25 (5) ◽

pp. 700-706 ◽

Cited By ~ 7

Author(s):

Katalin Ősz ◽

Katalin Várnagy ◽

Imre Sóvágó ◽

Lídia Lennert ◽

Helga Süli-Vargha ◽

...

Keyword(s):

Amino Acid ◽

Transition Metal ◽

Metal Complexes ◽

Transition Metal Complexes ◽

Amino Acid Derivatives ◽

Structural Studies

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Chiral donor–acceptor azetines as powerful reactants for synthesis of amino acid derivatives

Nature Communications ◽

10.1038/s41467-019-13326-8 ◽

2019 ◽

Vol 10 (1) ◽

Cited By ~ 2

Author(s):

Kostiantyn O. Marichev ◽

Kuiyong Dong ◽

Lynée A. Massey ◽

Yongming Deng ◽

Luca De Angelis ◽

...

Keyword(s):

Amino Acid ◽

Amino Acid Derivatives ◽

Coupling Reactions ◽

Central Importance ◽

Bond Forming ◽

Donor Acceptor ◽

High Yields ◽

High Degree ◽

Oxygen Bond ◽

Steric Selectivity

AbstractCoupling reactions of amines and alcohols are of central importance for applications in chemistry and biology. These transformations typically involve the use of a reagent, activated as an electrophile, onto which nucleophile coupling results in the formation of a carbon-nitrogen or a carbon–oxygen bond. Several promising reagents and procedures have been developed to achieve these bond forming processes in high yields with excellent stereocontrol, but few offer direct coupling without the intervention of a catalyst. Herein, we report the synthesis of chiral donor–acceptor azetines by highly enantioselective [3 + 1]-cycloaddition of enoldiazoacetates with aza-ylides and their selective coupling with nitrogen and oxygen nucleophiles via 3-azetidinones to form amino acid derivatives, including those of peptides and natural products. The overall process is general for a broad spectrum of nucleophiles, has a high degree of electronic and steric selectivity, and retains the enantiopurity of the original azetine.

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