scholarly journals Dirhodium(II)-Catalyzed Synthesis of N-(Arylsulfonyl)hydrazines by N–H Amination of Aliphatic Amines

Synlett ◽  
2022 ◽  
Author(s):  
Motoki Ito ◽  
Shigeo Sugiyama ◽  
Yui Hasegawa ◽  
Satomi Saito ◽  
Asami Onda ◽  
...  
Keyword(s):  
Amino Acid ◽  
Aliphatic Amines ◽  
Amino Acid Derivatives ◽  
First Report ◽  
Hydrazine Derivatives ◽  
Bond Forming ◽  
Combined Use

AbstractThis study reports the development of Rh(II)-catalyzed N–N bond-forming reaction of amino acid derivatives or aliphatic amines to provide hydrazine derivatives through the combined use of Rh2(esp)2 and [(3,4-dimethoxyphenyl)sulfonylimino]-2,4,6-trimethylphenyliodinane (3,4-(MeO)2C6H3SO2N=IMes). This is the first report of N–H amination of aliphatic amines with metal–nitrene species.

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

2019 ◽  
Vol 10 (1) ◽  
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.

scholarly journals Application of Polyamines and Amino Acid Derivatives Based on 2-Azabicycloalkane Backbone in Enantioselective Aldol Reaction

Molecules ◽  
2021 ◽  
Vol 26 (17) ◽  
pp. 5166
Author(s):  
Dominika Iwan ◽  
Karolina Kamińska ◽  
Elżbieta Wojaczyńska
Keyword(s):  
Catalytic Activity ◽  
Amino Acid ◽  
Aldol Reaction ◽  
Aqueous Media ◽  
Amino Acid Derivatives ◽  
Carbon Bond ◽  
Bond Forming ◽  
Backbone Amide ◽  
Carbon Carbon Bond ◽  
Excellent Chemical

Carbon–carbon bond forming reactions, such as aldol reaction and condensation, belong to extremely desired transformations as manifested by >25,000 entries in SciFinder. Their stereoselective variant requires the use of an appropriate catalyst with a strictly defined structure. Hence, chiral 2-azabicycloalkane-based catalysts were designed, synthesized and tested in a stereoselective aldol reaction between cyclic/acyclic ketone and p-nitrobenzaldehyde both in organic and aqueous media. Among catalysts containing a chiral bicyclic backbone, amide based on 2-azabicyclo[3.2.1]octane and pyrrolidine units showed the best catalytic activity and afforded aldol product in excellent chemical yields (up to 95%) and good diastereo- and enantioselectivity (dr 22:78, ee up to 63%).

Highly enantioselective carbene insertion into N–H bonds of aliphatic amines

Science ◽  
2019 ◽  
Vol 366 (6468) ◽  
pp. 990-994 ◽  
Author(s):  
Mao-Lin Li ◽  
Jin-Han Yu ◽  
Yi-Hao Li ◽  
Shou-Fei Zhu ◽  
Qi-Lin Zhou
Keyword(s):  
Amino Acid ◽  
Copper Complex ◽  
Transition Metal Catalysts ◽  
Aliphatic Amines ◽  
Amino Acid Derivatives ◽  
Insertion Reactions ◽  
Insertion Product ◽  
Carbene Insertion ◽  
Diazo Esters ◽  
Copper Center

Aliphatic amines strongly coordinate, and therefore easily inhibit, the activity of transition-metal catalysts, posing a marked challenge to nitrogen-hydrogen (N–H) insertion reactions. Here, we report highly enantioselective carbene insertion into N–H bonds of aliphatic amines using two catalysts in tandem: an achiral copper complex and chiral amino-thiourea. Coordination by a homoscorpionate ligand protects the copper center that activates the carbene precursor. The chiral amino-thiourea catalyst then promotes enantioselective proton transfer to generate the stereocenter of the insertion product. This reaction couples a wide variety of diazo esters and amines to produce chiral α-alkyl α–amino acid derivatives.

scholarly journals Enantioselective Synthesis of anti-β-Hydroxy-α-amino Esters via an Organocatalyzed Decarboxylative Aldol Reaction

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1295-1299 ◽  
Author(s):  
Yoshiji Takemoto ◽  
Taryn March ◽  
Akihiro Murata ◽  
Yusuke Kobayashi
Keyword(s):  
Amino Acid ◽  
Malonic Acid ◽  
Aldol Reaction ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives ◽  
Amino Esters ◽  
Combined Use ◽  
Aldol Addition ◽  
High Yields ◽  
Pentafluorobenzoic Acid

The first enantioselective decarboxylative aldol addition with α-amido-substituted malonic acid half oxyesters (MAHOs) is described. The combined use of a newly designed bifunctional sulfonamide catalyst with pentafluorobenzoic acid as an additive afforded the β-hydroxy-α-amino acid derivatives in moderate to high yields and with high enantioselectivities.

Three Amino Acid Derivatives of Valproic Acid: Design, Synthesis, Theoretical and Experimental Evaluation as Anticancer Agents

2014 ◽  
Vol 14 (7) ◽  
pp. 984-993 ◽  
Author(s):  
Gabriela Luna-Palencia ◽  
Federico Martinez-Ramos ◽  
Ismael Vasquez-Moctezuma ◽  
Manuel Fragoso-Vazquez ◽  
Jessica Mendieta-Wejebe ◽  
...  
Keyword(s):  
Valproic Acid ◽  
Amino Acid ◽  
Anticancer Agents ◽  
Experimental Evaluation ◽  
Amino Acid Derivatives ◽  
Design Synthesis ◽  
Derivatives Of

scholarly journals In vitro anticancer potentiality and molecular modelling study of novel amino acid derivatives based on N1,N3-bis-(1-hydrazinyl-1-oxopropan-2-yl) isophthalamide

2019 ◽  
Vol 34 (1) ◽  
pp. 1247-1258 ◽  
Author(s):  
Asmaa F. Kassem ◽  
Gaber O. Moustafa ◽  
Eman S. Nossier ◽  
Hemat S. Khalaf ◽  
Marwa M. Mounier ◽  
...  
Keyword(s):  
Amino Acid ◽  
Molecular Modelling ◽  
Amino Acid Derivatives ◽  
Modelling Study

scholarly journals Synthesis and antimicrobial activity of some novel 1,2-dihydro-[1,2,4]triazolo[1,5-a]pyrimidines bearing amino acid moiety

RSC Advances ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 2905-2916
Author(s):  
Mounir A. A. Mohamed ◽  
Adnan A. Bekhit ◽  
Omyma A. Abd Allah ◽  
Asmaa M. Kadry ◽  
Tamer M. Ibrahim ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Amino Acid ◽  
Green Chemistry ◽  
Antimicrobial Activities ◽  
Amino Acid Derivatives ◽  
Acid Moiety ◽  
Amino Acid Moiety

A new series of [1,2,4]-triazole bearing amino acid derivatives were synthesized under green chemistry conditions and evaluated for their antimicrobial activities.

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