Enantio‐ and Diastereoselective Synthesis of β‐Aryl‐β‐pyrazolyl α‐Amino Acid Esters via Copper‐Catalyzed Reaction of Azomethine Ylides with Benzylidenepyrazolones

2019 ◽  
Vol 361 (6) ◽  
pp. 1389-1393 ◽  
Author(s):  
Yan‐Chuan Gong ◽  
Yue Wang ◽  
Er‐Qing Li ◽  
Hao Cui ◽  
Zheng Duan
Keyword(s):  
Amino Acid ◽  
Azomethine Ylides ◽  
Amino Acid Esters ◽  
Diastereoselective Synthesis ◽  
Acid Esters

Diastereoselective 1,3-Dipolar Cycloadditions and Michael Reactions of Azomethine Ylides to (2R)-3-Benzoyl-4-methylidene-2-phenyloxazolidin-5-one and (2S)-3-Benzoyl-2-t-butyl-4-methylideneoxazolidin-5-one

1998 ◽  
Vol 51 (2) ◽  
pp. 137 ◽  
Author(s):  
Stephen G. Pyne ◽  
Javad Safaei-G. ◽  
Karl Schafer ◽  
Abdollah Javidan ◽  
Brian W. Skelton ◽  
...  
Keyword(s):  
Amino Acid ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Amino Acid Esters ◽  
Dipolar Cycloadditions ◽  
Michael Reactions ◽  
Michael Adducts ◽  
Practical Synthesis ◽  
The Michael Addition ◽  
Acid Esters

The 1,3-dipolar cycloaddition reactions of (1) and (11) with the azomethine ylides derived from N-benzylidene α-amino acid esters (2) proceed with good to high exo-diastereoselectivity giving the cycloadducts (4) and (12), respectively. The cycloaddition adducts can be converted to highly functionalised prolines (14), (15) and (17) in high enantiomeric purities. The Michael addition adducts of (1) and (11) with the azomethine ylides derived from the N-(disubstituted methylidene) α-amino acid esters (18), (19) and (33) allow for a practical synthesis of all four stereoisomers of 4-benzamidopyroglutamate. The stereochemistry of these cycloaddition and Michael adducts has been extensively determined by single-crystal X-ray structural analysis [compounds (4b), (5b,d), (12b,d), (13e), (15), (20), (21) and (27)]. Lithium-chelated transition state structures have been proposed to rationalize the stereochemical outcomes of these reactions.

ChemInform Abstract: Diastereoselective Synthesis of N-(α-Aryl-α-haloacetyl) Amino Acid Esters by Acylation Using 3-Aryl-2,2-dicyanooxiranes.

ChemInform ◽  
2010 ◽  
Vol 30 (48) ◽  
pp. no-no
Author(s):  
Florence Roger ◽  
Marie-Gabrielle Le Pironnec ◽  
Michel Guerro ◽  
Patrick Gougeon ◽  
Philippe Gall ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Acid Esters ◽  
Diastereoselective Synthesis ◽  
Acid Esters

Asymmetric Preparation of anti-β-Hydroxyα-amino Acid Esters

Synfacts ◽  
2006 ◽  
Vol 2006 (12) ◽  
pp. 1253-1253
Author(s):  
Y. Hamada ◽  
K. Makino ◽  
M. Iwasaki
Keyword(s):  
Amino Acid ◽  
Amino Acid Esters ◽  
Acid Esters

Antiviral activity of glycyrrhizic acid conjugates with amino acid esters against Zika virus

2021 ◽  
Vol 294 ◽  
pp. 198290
Author(s):  
Lidia A. Baltina ◽  
Mann-Jen Hour ◽  
Ya-Chi Liu ◽  
Young-Sheng Chang ◽  
Su-Hua Huang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Antiviral Activity ◽  
Zika Virus ◽  
Glycyrrhizic Acid ◽  
Amino Acid Esters ◽  
Acid Esters
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