Improved Preparation of Enantiomerically Pure 5-Oxo Amino Acid Derivatives by Palladium-Catalysed Coupling Reactions

Synlett ◽  
1995 ◽  
Vol 1995 (08) ◽  
pp. 819-820 ◽  
Author(s):  
Joanne L. Fraser ◽  
Richard F. W. Jackson ◽  
Barry Porter
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Coupling Reactions ◽  
Enantiomerically Pure

Peptide deformylase as biocatalyst for the synthesis of enantiomerically pure amino acid derivatives

2004 ◽  
Vol 29 (1-6) ◽  
pp. 265-277 ◽  
Author(s):  
Theo Sonke ◽  
Bernard Kaptein ◽  
A.F.Volker Wagner ◽  
Peter J.L.M Quaedflieg ◽  
Sabine Schultz ◽  
...  
Keyword(s):  
Amino Acid ◽  
Peptide Deformylase ◽  
Amino Acid Derivatives ◽  
Enantiomerically Pure ◽  
Pure Amino Acid

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.

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.

Novel Acetoxylation and C−C Coupling Reactions at Unactivated Positions in α-Amino Acid Derivatives

2006 ◽  
Vol 8 (15) ◽  
pp. 3391-3394 ◽  
Author(s):  
B. V. Subba Reddy ◽  
Leleti Rajender Reddy ◽  
E. J. Corey
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Coupling Reactions

scholarly journals Asymmetric Synthesis of α,α-Difluoro-β-amino Acid Derivatives from Enantiomerically Pure N-tert-Butylsulfinimines.

ChemInform ◽  
2003 ◽  
Vol 34 (16) ◽  
Author(s):  
Donnette D. Staas ◽  
Kelly L. Savage ◽  
Carl F. Homnick ◽  
Nancy N. Tsou ◽  
Richard G. Ball
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Amino Acid Derivatives ◽  
Enantiomerically Pure
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