Enantioselective Synthesis of Allylic Alcohols via an Oxazaborolidinium Ion Catalyzed Diels−Alder/Retro-Diels−Alder Sequence

2009 ◽  
Vol 11 (22) ◽  
pp. 5358-5361 ◽  
Author(s):  
Simon Jones ◽  
Damien Valette
Keyword(s):  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Allylic Alcohols

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.

A Diels-Alder/Retro-Diels-Alder Approach for the Enantioselective Synthesis of Microbial Butenolides

2012 ◽  
pp. n/a-n/a ◽  
Author(s):  
Christian A. Citron ◽  
Susanne M. Wickel ◽  
Barbara Schulz ◽  
Siegfried Draeger ◽  
Jeroen S. Dickschat
Keyword(s):  
Diels Alder ◽  
Enantioselective Synthesis
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