ChemInform Abstract: ON THE INTERACTIVITY OF CHIRAL AUXILIARIES WITH CHIRAL CATALYSTS IN THE HETERO DIELS-ALDER REACTION: A NEW ROUTE TO L-GLYCOLIPIDS

1984 ◽  
Vol 15 (9) ◽  
Author(s):  
M. BEDNARSKI ◽  
S. DANISHEFSKY
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Auxiliaries ◽  
Chiral Catalysts ◽  
Diels Alder Reaction

Synthesis and evaluation of 7-hydroxyindan-1-one-derived chiral auxiliaries

2005 ◽  
Vol 83 (5) ◽  
pp. 413-419 ◽  
Author(s):  
Arun A Narine ◽  
Peter D Wilson
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Auxiliaries ◽  
Diels Alder Reaction ◽  
High Degree

A series of novel chiral acetals were prepared from 7-hydroxyindan-1-one and a variety of substituted chiral nonracemic C2-symmetric 1,2-ethanediols (R = Me, Ph, CH2OMe, CH2OBn, CH2O(1-Np), and i-Pr). These acetals were evaluated as chiral auxiliaries for use in asymmetric synthesis. A high degree of stereochemical induction was observed in the diethylaluminum chloride-promoted Diels–Alder reaction of an acrylate derivative (R = i-Pr) with cyclopentadiene (91:9 dr). This demonstrated that these acetals could serve as effective chiral directors in asymmetric substrate-directed reactions.Key words: 7-hydroxyindan-1-one, chiral nonracemic C2-symmetric 1,2-diols, acetals, chiral auxiliaries, Diels–Alder reaction.

Asymmetric Diels-Alder reaction of cyclopentadiene with methacrolein using polymer-supported chiral catalysts

1995 ◽  
Vol 24 (3) ◽  
pp. 219-227 ◽  
Author(s):  
Shinichi Itsuno ◽  
Katsuhiro Watanabe ◽  
Takahiro Koizumi ◽  
Koichi Ito
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Catalysts ◽  
Diels Alder Reaction ◽  
Polymer Supported

π-Stacking Effect on Levoglucosenone Derived Internal Chiral Auxiliaries. A Case of Complete Enantioselectivity Inversion on the Diels−Alder Reaction

2008 ◽  
Vol 10 (16) ◽  
pp. 3389-3392 ◽  
Author(s):  
Ariel M. Sarotti ◽  
Israel Fernández ◽  
Rolando A. Spanevello ◽  
Miguel Á. Sierra ◽  
Alejandra G. Suárez
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Auxiliaries ◽  
Diels Alder Reaction ◽  
Π Stacking ◽  
Stacking Effect

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.

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