ChemInform Abstract: Introduction of Carbocycles and Heterocycles in the Side Chain of . alpha.-Trifluoromethyl-Substituted α-Amino Acids via Diels-Alder Reaction.

ChemInform ◽  
2010 ◽  
Vol 23 (19) ◽  
pp. no-no
Author(s):  
K. BURGER ◽  
K. GAA ◽  
K. MUETZE
Keyword(s):  
Amino Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Side Chain ◽  
Diels Alder Reaction

A diastereoselective aza-Diels–Alder reaction of N-aryl-1-azadienes derived from α-amino acids with enamines

2011 ◽  
Vol 52 (32) ◽  
pp. 4109-4111 ◽  
Author(s):  
Javier Vicario ◽  
Domitila Aparicio ◽  
Francisco Palacios
Keyword(s):  
Amino Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

scholarly journals Natural amino acids as chiral auxiliaries in asymmetric Diels–Alder reactions

1988 ◽  
Vol 66 (11) ◽  
pp. 2826-2829 ◽  
Author(s):  
Maria P. Bueno ◽  
Carlos Cativiela ◽  
José A. Mayoral ◽  
Alberto Avenoza ◽  
Paula Charro ◽  
...  
Keyword(s):  
Amino Acids ◽  
Structural Similarity ◽  
Alder Reaction ◽  
Diels Alder ◽  
Isopropyl Ester ◽  
Chiral Auxiliaries ◽  
Titanium Catalysts ◽  
Diels Alder Reaction ◽  
Catalyzed Reactions ◽  
Natural Amino Acids

To test whether α-amino acids can be efficient chiral auxiliaries in asymmetric Diels–Alder reactions, the chiral dienophile N-acryloyl-L-phenylalanine methyl ester was made to react with cyclopentadiene. Diastereofacial selectivity is to a great extent dependent on the Lewis acid used to promote the reaction; whereas moderate excesses of the (1R,2R)-cycloadduct were achieved with AlCl3, the reaction did not show diastereofacial selectivity when titanium catalysts were used. Moreover, with Ti(iPrO)4 a transesterification reaction, which leads to the isopropyl ester and competes with the Diels–Alder reaction, was observed. In spite of the structural similarity of this dienophile to the acrylate of (S)-ethyl lactate, it behaved very differently in the titanium-catalyzed reactions.

Total synthesis of mycophenolic acid

1997 ◽  
Vol 75 (6) ◽  
pp. 641-645 ◽  
Author(s):  
Ricardo A. de la Cruz ◽  
Francisco X. Talamás ◽  
Alfredo Vázquez ◽  
Joseph M. Muchowski
Keyword(s):  
Total Synthesis ◽  
Mycophenolic Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Side Chain ◽  
Diels Alder Reaction

A total synthesis of mycophenolic acid is reported. Diels–Alder reaction of [5-methoxy-3-(1-methoxypropenyl)-4,5-dihydrofuran-2-yloxy]-trimethylsilane with 3-benzenesulfinyl-5H-furan-2-one afforded the hexasubstituted nucleus. The side chain was constructed from the unveiled aldehyde. Keywords: mycophenolic acid, Diels–Alder reaction, pentasubstituted diene.

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