Room-Temperature Polycondensation of β-Amino Acid Derivatives. IV. Solvent Effect on the Michael Reaction of Acrylates

1968 ◽  
Vol 41 (8) ◽  
pp. 1968-1970 ◽  
Author(s):  
Kohei Sanui ◽  
Naoya Ogata
Keyword(s):  
Amino Acid ◽  
Solvent Effect ◽  
Room Temperature ◽  
Michael Reaction ◽  
Amino Acid Derivatives ◽  
The Michael Reaction

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.

N-Methylamino acids in peptide synthesis. V. The synthesis of N-tert-butyloxycarbonyl, N-methylamino acids by N-methylation

1977 ◽  
Vol 55 (5) ◽  
pp. 906-910 ◽  
Author(s):  
S. T. Cheung ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Methyl Iodide ◽  
Peptide Synthesis ◽  
Room Temperature ◽  
Sodium Hydride ◽  
Amino Acid Derivatives ◽  
Enantiomerically Pure ◽  
Neutral Amino Acids ◽  
Related Data

The preparation of enantiomerically pure N-tert-butyloxycarbonyl,N-methylamino acids by N-methylation of the parent amino acid derivatives using sodium hydride and methyl iodide in tetrahydrofuran at room temperature is described for neutral amino acids including O-benzyl-protected threonine and tyrosine. Methylation of the O-benzylserine derivative under these conditions gives the N-methyldehydroalanine derivative. The β-elimination is completely suppressed, giving the corresponding N-methylserine derivative when the reaction is carried out at 5 °C. Other related data on N-methylation and N-methylamino acid derivatives are presented.

Efficient Enantioselective Michael Addition of Nitroalkenes Catalyzed by a New Surfactant-Type Thiourea Organocatalyst in Water

2014 ◽  
Vol 1015 ◽  
pp. 602-605 ◽  
Author(s):  
Hong Ying Zhang ◽  
Xue Ming Yan
Keyword(s):  
Michael Addition ◽  
Room Temperature ◽  
Michael Reaction ◽  
The Michael Reaction

A new surfactant-type bifunctional thiourea organocatalysts were synthesized. In the presence of 10 mol% PhCOOH, the Michael reaction of nitroalkenes with various nucleophiles could be catalyzed smoothly by this new organocatalyst in water at room temperature, giving the desired adducts in good yields with high diastereoselectivities (syn/anti=82/18->99/1) and excellent enantioselectivities (up to 97% ee)

Diastereoselectivity in the Synthesis of Unnatural α-Amino Acid Esters by Phase Transfer Catalysis

2004 ◽  
Vol 59 (3) ◽  
pp. 305-309 ◽  
Author(s):  
Francisco Furtado Tavares Lins ◽  
Lázaro Pereira da Cunha ◽  
Yvone Brígido Memória Pouliquen ◽  
Telma Leda Gomes Lemos ◽  
Marcos Carlos de Mattos
Keyword(s):  
Amino Acid ◽  
Michael Reaction ◽  
Phase Transfer ◽  
Progressive Increase ◽  
Amino Acid Esters ◽  
Catalytic Condition ◽  
Michael Acceptors ◽  
Diastereomeric Excess ◽  
Acid Esters ◽  
The Michael Reaction

Two unnatural α-amino acid esters were prepared in good yields via phase transfer catalyzed Michael addition of ethyl N-acetylaminocyanoacetate to chalcone and benzalketone. For both α- enones, a progressive increase in product diastereomeric excess (d.e.) was observed during the course of reaction, even in the absence of quaternary ammonium salt. However, for a fixed reaction time, higher d.e. values were obtained under phase transfer catalytic condition. Analogous reactions were performed using S-aryl thiocinnamates as Michael acceptors, affording a 2-pyrrolidinone in good yield but low d.e. These results were interpreted on the basis of the reversibility of the Michael reaction

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