γ-FLUOROGLUTAMIC ACID

1962 ◽  
Vol 40 (8) ◽  
pp. 1571-1575 ◽  
Author(s):  
R. L. Buchanan ◽  
F. H. Dean ◽  
F. L. M. Pattison
Keyword(s):  
Amino Acid ◽  
Michael Reaction ◽  
Mild Conditions ◽  
The Michael Reaction

The synthesis of γ-fluoroglutamic acid, HOOCCHFCH2CH(NH2)COOH, was achieved by two independent methods, both of which involved the Michael reaction: (1) methyl α-fluoroacrylate and diethyl acetamidomalonate gave the transesterified intermediate, which on hydrolysis produced γ-fluoroglutamic acid (31% yield); (2) ethyl α-acetamidoacrylate and diethyl fluoromalonate reacted under mild conditions to give, after hydrolysis, the required amino acid in 56% overall yield. Of the two procedures, the second is preferable, since it is based on more readily available starting materials and gives a higher yield.

The solvent-controlled chemoselective construction of C–S/S–S bonds via the Michael reaction/thiol coupling of quinoline-2-thiones

2019 ◽  
Vol 17 (9) ◽  
pp. 2379-2383 ◽  
Author(s):  
Xi Zhang ◽  
Tong-Lin Wang ◽  
Xiao-Jun Liu ◽  
Xi-Cun Wang ◽  
Zheng-Jun Quan
Keyword(s):  
Michael Reaction ◽  
Mild Conditions ◽  
The Michael Reaction

The solvent-controlled selective construction of C–S and S–S bonds containing a quinoline skeleton under mild conditions from quinoline-2-thiones has been reported.

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

Sterically hindered 1,3-diketones in the Michael reaction

1996 ◽  
Vol 45 (1) ◽  
pp. 137-139
Author(s):  
I. E. Sokolov ◽  
A. S. Zanina ◽  
S. I. Shergina ◽  
M. S. Shvartsberg
Keyword(s):  
Michael Reaction ◽  
Sterically Hindered ◽  
The Michael Reaction

The Michael Reaction

2002 ◽  
Vol 79 (2) ◽  
pp. 264 ◽  
Author(s):  
Thomas Poon ◽  
Bradford P. Mundy ◽  
Thomas W. Shattuck
Keyword(s):  
Michael Reaction ◽  
The Michael Reaction

Synthesis of New Chiral 4,5,6,7-Tetrahydro[1,2,3]triazolo[1,5-a]pyrazines from α-Amino Acid Derivatives under Mild Conditions.

ChemInform ◽  
2007 ◽  
Vol 38 (48) ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Pradip K. Maity ◽  
Rajesh G. Gonnade ◽  
Mukund S. Chorghade ◽  
Mukund K. Gurjar
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Mild Conditions

scholarly journals Preparation of Polyamines by the Michael Reaction

1968 ◽  
Vol 41 (10) ◽  
pp. 2519-2521 ◽  
Author(s):  
Kentaro Yoda ◽  
Takao Toda
Keyword(s):  
Michael Reaction ◽  
The Michael Reaction
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