Selective cleavage of the allyl and (allyloxy)carbonyl groups through palladium-catalyzed hydrostannolysis with tributyltin hydride. Application to the selective protection-deprotection of amino acid derivatives and in peptide synthesis

1987 ◽  
Vol 52 (22) ◽  
pp. 4984-4993 ◽  
Author(s):  
O. Dangles ◽  
F. Guibe ◽  
G. Balavoine ◽  
S. Lavielle ◽  
A. Marquet
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Amino Acid Derivatives ◽  
Carbonyl Groups ◽  
Selective Protection ◽  
Tributyltin Hydride ◽  
Palladium Catalyzed

Solution phase peptide synthesis with ferrocenyl amino acid derivatives

2001 ◽  
Vol 637-639 ◽  
pp. 349-355 ◽  
Author(s):  
Jan Sehnert ◽  
Alexandra Hess ◽  
Nils Metzler-Nolte
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Solution Phase ◽  
Amino Acid Derivatives

Palladium‐Catalyzed Allylic Alkylation of Aldimine Esters with Vinyl‐Cyclopropanes to Yield α,α‐Disubstituted α‐Amino Acid Derivatives

2019 ◽  
Vol 361 (22) ◽  
pp. 5105-5111 ◽  
Author(s):  
Jiahua Wang ◽  
Zonghao Dai ◽  
Cheng Xiong ◽  
Jin Zhu ◽  
Jinrong Lu ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Allylic Alkylation ◽  
Palladium Catalyzed

Reaction of N-Benzoyl-2-bromoglycine Methyl Ester With Deprotonated Nitroalkanes: Synthesis of β-Nitro and α,β-Dehydro Amino Acid Derivatives

1988 ◽  
Vol 41 (7) ◽  
pp. 1063 ◽  
Author(s):  
VA Burgess ◽  
CJ Easton
Keyword(s):  
Amino Acid ◽  
Methyl Ester ◽  
Amino Acid Derivatives ◽  
Tributyltin Hydride ◽  
Acid Hydrochloride ◽  
Elimination Reactions ◽  
Diaminopropionic Acid

N-Benzoyl-2-bromoglycine methyl ester (1) reacted with the alkyl nitronates (2a-e) to give the corresponding β-nitro amino acid derivatives (4a-e). Elimination reactions of (4a-d) afforded the α,β-dehydro amino acid derivatives (5a-d). Treatment of the β- nitrovaline derivative (4b) with tributyltin hydride gave the valine derivative (8). Reduction of the β- nitroalanine derivative (4a) gave the β- aminoalanine derivative (9), characterized by hydrolysis to 2,3- diaminopropionic acid hydrochloride.

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.

Palladium-Catalyzed Intermolecular Aminocarbonylation of Alkenes: Efficient Access of β-Amino Acid Derivatives

2015 ◽  
Vol 137 (7) ◽  
pp. 2480-2483 ◽  
Author(s):  
Jiashun Cheng ◽  
Xiaoxu Qi ◽  
Ming Li ◽  
Pinhong Chen ◽  
Guosheng Liu
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Efficient Access ◽  
Palladium Catalyzed
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