Concise enantioselective synthesis of wine lactone via intramolecular Diels–Alder reaction

2021 ◽  
Author(s):  
Yasutaka Ohkubo ◽  
Yui Masuda ◽  
Yusuke Ogura ◽  
Hirosato Takikawa ◽  
Hidenori Watanabe
Keyword(s):  
White Wine ◽  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Diels Alder Reaction ◽  
Butenoic Acid ◽  
Citrus Juices

Abstract An enantioselective synthesis of (3S,3aS,7aR)-wine lactone, a major aroma component of white wine and citrus juices, was achieved starting from (S)-2-methyl-3-butenoic acid. An intramolecular Diels–Alder reaction was employed as a key step.

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.

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

The use of (−)-8-phenylisoneomenthol and (−)-8-phenylmenthol in the enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]heptane derivatives via aza-Diels–Alder reaction

Tetrahedron ◽  
2006 ◽  
Vol 62 (40) ◽  
pp. 9475-9482 ◽  
Author(s):  
Maria Luísa Cardoso do Vale ◽  
José Enrique Rodríguez-Borges ◽  
Olga Caamaño ◽  
Franco Fernández ◽  
Xerardo García-Mera
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Diels Alder Reaction

Enantioselective Synthesis of Highly Functionalized 4-Piperidones by the Asymmetric Imino-Diels–Alder Reaction of Chiral 2-Amino-1,3-Butadienes

1996 ◽  
Vol 2 (7) ◽  
pp. 805-811 ◽  
Author(s):  
José Barluenga ◽  
Fernando Aznar ◽  
Cristina Ribas ◽  
Carlos Valdés ◽  
Monica Fernández ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Diels Alder Reaction

Catalytic Enantioselective Synthesis of 2,6-Disubstituted Dihydropyrones by Hetero-Diels-Alder Reaction Using Chiral BINOL-Ti(IV) Complex

Synlett ◽  
2002 ◽  
pp. 2122-2124 ◽  
Author(s):  
Xiaoming Feng ◽  
Yaozhong Jiang ◽  
Yaozong Huang ◽  
Bin Wang ◽  
Guolin Zhang
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Diels Alder Reaction
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