Synthesis of Conformationally ConstrainedC-Glycosyl α- and β-Amino Acids and Sugar−Carbamino Sugar Hybrids via Diels−Alder Reaction†

2005 ◽  
Vol 7 (24) ◽  
pp. 5441-5444 ◽  
Author(s):  
K. Jayakanthan ◽  
Yashwant D. Vankar
Keyword(s):  
Amino Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
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.

Aza-Diels–Alder reaction of α,β-unsaturated sulfinylimines derived from α-amino acids with enolethers and enamines

2007 ◽  
Vol 48 (38) ◽  
pp. 6747-6750 ◽  
Author(s):  
Francisco Palacios ◽  
Javier Vicario ◽  
Domitila Aparicio
Keyword(s):  
Amino Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Asymmetric synthesis of bicyclic α-amino acids by a Diels–Alder reaction to a new chiral α,β-didehydroalanine derivative

1999 ◽  
Vol 10 (5) ◽  
pp. 821-825 ◽  
Author(s):  
Rafael Chinchilla ◽  
Larry R Falvello ◽  
Nuria Galindo ◽  
Carmen Nájera
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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