Asymmetric Lewis Acid-Catalyzed Diels−Alder Reactions of α,β-Unsaturated Ketones and α,β-Unsaturated Acid Chlorides

2003 ◽  
Vol 5 (23) ◽  
pp. 4293-4295 ◽  
Author(s):  
Joel M. Hawkins ◽  
Mitch Nambu ◽  
Stefan Loren
Keyword(s):  
Lewis Acid ◽  
Unsaturated Acid ◽  
Diels Alder ◽  
Acid Chlorides ◽  
Unsaturated Ketones ◽  
Acid Catalyzed

Ruthenium–Lewis Acid Catalyzed Asymmetric Diels–Alder Reactions between Dienes and α,β-Unsaturated Ketones

2007 ◽  
Vol 13 (12) ◽  
pp. 3354-3368 ◽  
Author(s):  
Jenny Rickerby ◽  
Martial Vallet ◽  
Gerald Bernardinelli ◽  
Florian Viton ◽  
E. Peter Kündig
Keyword(s):  
Lewis Acid ◽  
Diels Alder ◽  
Unsaturated Ketones ◽  
Acid Catalyzed

Lewis acid catalyzed Diels–Alder reactions of two useful dienyl phosphate esters

1994 ◽  
Vol 72 (10) ◽  
pp. 2163-2175 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Waiseng Martin Feng ◽  
Jeung Bea Kim ◽  
Eric N.C. Browne
Keyword(s):  
Lewis Acid ◽  
Diels Alder ◽  
Vinyl Ketone ◽  
Phosphate Esters ◽  
Stannic Chloride ◽  
Ethyl Vinyl ◽  
Methyl Vinyl ◽  
Unsaturated Ketones ◽  
Acid Catalyzed ◽  
Cyclohexene Derivatives

The Lewis acid catalyzed Diels–Alder reactions of dienyl phosphate esters 1 and 2 were examined. 2-Diethylphosphoryloxy-1,3-butadiene (1) was found to react with a variety of α,β-unsaturated carbonyl compounds under Lewis acid catalysis with excellent regioselectivity to give synthetically useful cyclohexene derivatives. The adducts were produced in accordance with the normal rules governing the Diels–Alder addition. In the presence of stannic chloride acyclic α,β-unsaturated ketones such as ethyl vinyl ketone and methyl vinyl ketone reacted rapidly with diene phosphate 1 to give exclusively the para-addition products 8 and 9 in excellent yields. When diene 1 was treated with the complex cyclic enone ester 14 in the presence of ferric chloride the single para-rule adduct 15 was obtained in good yield. The stannic chloride catalyzed Diels–Alder reactions of trans-2-diethylphosphoryloxy-1,3-pentadiene (2) were also studied. Diene phosphate 2 reacted efficiently with a number of acyclic α,β-unsaturated ketones such as methyl vinyl ketone, ethyl vinyl ketone, and trans-3-penten-2-one with complete regio- and stereoselectivity to give single cyclohexene derivatives 38, 39, and 40.

Ruthenium—Lewis Acid Catalyzed Asymmetric Diels—Alder Reactions Between Dienes and α,β-Unsaturated Ketones.

ChemInform ◽  
2007 ◽  
Vol 38 (33) ◽  
Author(s):  
Jenny Rickerby ◽  
Martial Vallet ◽  
Gerald Bernardinelli ◽  
Florian Viton ◽  
E. Peter Kuendig
Keyword(s):  
Lewis Acid ◽  
Diels Alder ◽  
Unsaturated Ketones ◽  
Acid Catalyzed

Asymmetric synthesis of N-phenylethyl-2-phenyldecahydroquinolin-4-ones via Lewis acid catalyzed imino-Diels–Alder reaction

2000 ◽  
Vol 11 (12) ◽  
pp. 2509-2523 ◽  
Author(s):  
Renée Paugam ◽  
Emmanuelle Valenciennes ◽  
Linda Le Coz-Bardol ◽  
Jean-Christophe Garde ◽  
Lya Wartski ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Acid Catalyzed
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