Enantioselective synthesis of the bottom half of chlorothricolide. 2. A comparative study of substituent effects on the stereoselectivity of the key intramolecular Diels-Alder reaction

1988 ◽  
Vol 53 (3) ◽  
pp. 710-712 ◽  
Author(s):  
William R. Roush ◽  
Renata Riva
Keyword(s):  
Comparative Study ◽  
Substituent Effects ◽  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Diels Alder Reaction

Enantioselective Syntheses of Flavonoid Diels-Alder Natural Products: A Review

2018 ◽  
Vol 15 (2) ◽  
pp. 221-229 ◽  
Author(s):  
Shah Bakhtiar Nasir ◽  
Noorsaadah Abd Rahman ◽  
Chin Fei Chee
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Lewis Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Chiral Ligand ◽  
Asymmetric Syntheses ◽  
Diels Alder Reaction ◽  
Enantioselective Syntheses

Background: The Diels-Alder reaction has been widely utilised in the syntheses of biologically important natural products over the years and continues to greatly impact modern synthetic methodology. Recent discovery of chiral organocatalysts, auxiliaries and ligands in organic synthesis has paved the way for their application in Diels-Alder chemistry with the goal to improve efficiency as well as stereochemistry. Objective: The review focuses on asymmetric syntheses of flavonoid Diels-Alder natural products that utilize chiral ligand-Lewis acid complexes through various illustrative examples. Conclusion: It is clear from the review that a significant amount of research has been done investigating various types of catalysts and chiral ligand-Lewis acid complexes for the enantioselective synthesis of flavonoid Diels-Alder natural products. The results have demonstrated improved yield and enantioselectivity. Much emphasis has been placed on the synthesis but important mechanistic work aimed at understanding the enantioselectivity has also been discussed.

Synthetic and kinetic studies of substituent effects in the furan intramolecular Diels-Alder reaction

Tetrahedron ◽  
1994 ◽  
Vol 50 (23) ◽  
pp. 6767-6782 ◽  
Author(s):  
Brian J. McNelis ◽  
Daniel D. Sternbach ◽  
Andrew T. MacPhail
Keyword(s):  
Substituent Effects ◽  
Kinetic Studies ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Enantioselective synthesis of protected d-serine from tetrahydrooxazin-4-one via a hetero Diels–Alder reaction

2002 ◽  
Vol 13 (19) ◽  
pp. 2113-2115 ◽  
Author(s):  
Mauro Panunzio ◽  
Elisa Bandini ◽  
Eileen Campana ◽  
Paola Vicennati
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Diels Alder Reaction
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