scholarly journals Rhodium-catalyzed asymmetric addition of arylboronic acids to cyclic N-sulfonyl ketimines towards the synthesis of α,α-diaryl-α-amino acid derivatives

2015 ◽  
Vol 13 (17) ◽  
pp. 4918-4924 ◽  
Author(s):  
Ryosuke Takechi ◽  
Takahiro Nishimura
Keyword(s):  
Amino Acid ◽  
Ester Group ◽  
Amino Acid Derivatives ◽  
Asymmetric Addition ◽  
Arylboronic Acids ◽  
High Yields ◽  
Diene Complex

Rhodium/chiral diene complex-catalyzed asymmetric addition of arylboronic acids to cyclic ketimines having an ester group proceeded to give the corresponding α-amino acid derivatives in high yields with high enantioselectivity.

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽  
2022 ◽  
Author(s):  
Dishu Zeng ◽  
Tianbao Yang ◽  
Niu Tang ◽  
Wei Deng ◽  
Jiannan Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Efficient Method ◽  
Building Block ◽  
Room Temperature ◽  
Uv Light ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Plausible Mechanism ◽  
High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

Highly enantioselective synthesis of α-tertiary chiral amino acid derivatives through rhodium-catalyzed asymmetric arylation of cyclic N-sulfonyl α-ketimino esters

2018 ◽  
Vol 16 (25) ◽  
pp. 4633-4640 ◽  
Author(s):  
Zheng Wang ◽  
Ming-Hua Xu
Keyword(s):  
Amino Acid ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives ◽  
Arylboronic Acids

A simple sulfur-olefin ligand promoted Rh-catalyzed highly enantioselective arylation of cyclic α-ketimino esters with arylboronic acids is described.

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.

An Efficient Method for Constructing Cyclic β-Amino Acids Bearing Quaternary Stereocenters

Synlett ◽  
2019 ◽  
Vol 30 (05) ◽  
pp. 593-599 ◽  
Author(s):  
Shende Jiang ◽  
Guang Yang ◽  
Shuanglin Qin ◽  
Tongtong Liu ◽  
Yunhao Luo ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Efficient Method ◽  
Ester Group ◽  
Chiral Auxiliary ◽  
Allyl Ester ◽  
Stereogenic Centers ◽  
Quaternary Stereocenters ◽  
High Yields ◽  
Quaternary Stereogenic Centers

This paper describes an efficient method for constructing cyclic β-amino acids bearing quaternary stereocenters. NaHMDS-promoted asymmetric α-alkylation was employed to obtain the key intermediates with quaternary stereogenic centers, which were subsequently reduced by NaBH4 in 10% methanol in THF, with high yields and high diastereoselectivities. By removing the allyl ester group and the chiral auxiliary, the corresponding cyclic β-amino acid hydrochlorides were finally obtained.

Some N-acyl-D-amino acid derivatives having antibotulinal properties

1987 ◽  
Vol 33 (7) ◽  
pp. 577-582 ◽  
Author(s):  
A. Paquet ◽  
K. Rayman
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Aspartic Acid ◽  
Sodium Nitrite ◽  
Amino Acid Derivatives ◽  
Ester Method ◽  
Succinimidyl Ester ◽  
High Yields ◽  
Derivatives Of ◽  
Acyl Derivatives

Several N-acyl derivatives of D-tryptophan, D-alanine, D-methionine, D-valine, and D-aspartic acid were synthesized in high yields using the succinimidyl ester method and examined for their antibotulinal properties. In conjunction with 60 ppm of sodium nitrite, sorbyl-D-tryptophan, sorbyl-D-alanine, myristoyl-D-aspartic acid, and glycyl-D-alanine were highly inhibitory. In the absence of sodium nitrite, the N-acyl derivatives of the D-amino acids were not inhibitory. On its own, 60 ppm of sodium nitrite was only slightly inhibitory. Sorbyl-L-tryptophan and sorbyl-L-alanine had no effect in the presence or absence of 60 ppm of sodium nitrite.

A convenient synthesis of novel amino acid derivatives with potential antibacterial activity using sustainable materials

2017 ◽  
Vol 41 (5) ◽  
pp. 280-286
Author(s):  
Mohamed S. Behalo
Keyword(s):  
Antibacterial Activity ◽  
Amino Acid ◽  
Low Cost ◽  
Amino Acid Derivatives ◽  
Standard Drug ◽  
Chemical Structures ◽  
Coupling Reagent ◽  
Convenient Synthesis ◽  
Weak Activity ◽  
High Yields

Following the principles of green chemistry, cardanol derivatives have been used as renewable, low-cost and easily available natural starting materials to construct a variety of protected and unprotected amino acid derivatives. The reaction of cardanol derivatives with different phthalylamino acids including glycine, alanine, phenylalanine and valine in the presence of N,N′-dicyclohexylcarbodiimide (DCC) as coupling reagent yielded the target compounds in high yields. Deprotection of phthalylamino acid derivatives was achieved by heating with hydrazine hydrate. The chemical structures of all products were confirmed by spectral (FTIR, MS, 1H NMR, 13C NMR) and elemental analyses. The synthesised products were evaluated for their antibacterial activity, and the compounds exhibited potent to weak activity in comparison with a standard drug.

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