Enantioselective Synthesis of Allenylenol Silyl Ethers via Chiral Lithium Amide Mediated Reduction of Ynenoyl Silanes and Their Diels–Alder Reactions

2015 ◽  
Vol 17 (5) ◽  
pp. 1280-1283 ◽  
Author(s):  
Michiko Sasaki ◽  
Yasuhiro Kondo ◽  
Ta-ichi Moto-ishi ◽  
Masatoshi Kawahata ◽  
Kentaro Yamaguchi ◽  
...  
Keyword(s):  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Lithium Amide ◽  
Silyl Ethers ◽  
Mediated Reduction

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

Hydroisoquinoline Ring Construction via the Diels-Alder Reaction of Arecolone-derived Enole Silyl Ethers

Heterocycles ◽  
1994 ◽  
Vol 38 (7) ◽  
pp. 1609 ◽  
Author(s):  
Masako Nakagawa ◽  
Jian Ma ◽  
Yasuhiro Torisawa ◽  
Tohru Hino
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Silyl Ethers ◽  
Diels Alder Reaction

Enantioselective synthesis of α-hydroxy thioesters via oxazaborolidine-mediated reduction of α-phenylthio enones

1998 ◽  
Vol 39 (15) ◽  
pp. 2183-2186 ◽  
Author(s):  
Ramon Berenguer ◽  
Marta Cavero ◽  
Jordi Garcia ◽  
Montse Muñoz
Keyword(s):  
Enantioselective Synthesis ◽  
Mediated Reduction
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