Lewis Acid Catalyzed Intramolecular Diels−Alder Reactions of Acyclic (Z)-Substituted 1,3-Dienes

Lewis acid catalyzed intramolecular Diels−Alder reactions of trienes (E,E,Z)-1a − d, (E,E,Z)-4a − d, and (E,Z,Z)-7a,b are described. Trienes containing enal or enone dienophiles cyclize in excellent yield under mild conditions using substoichiometric amounts of MeAlCl2, in most cases with high level...

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Bibliographic Details
Published inOrganic letters Vol. 3; no. 6; pp. 957 - 960
Main Authors Yakelis, Neal A, Roush, William R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.03.2001
Amer Chemical Soc
Subjects
Acids, Acyclic - chemical synthesis
Acids, Acyclic - chemistry
Catalysis
Chemistry
Chemistry, Organic
Indicators and Reagents
Kinetics
Models, Molecular
Molecular Conformation
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
REARRANGEMENT
TAXANE RING
(Z)-DIENE
STEREOCHEMICAL CONTROL
DIENE
ISOMERIZATION
CYTOCHALASIN SUPPORT
ALKALOIDS
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Summary:Lewis acid catalyzed intramolecular Diels−Alder reactions of trienes (E,E,Z)-1a − d, (E,E,Z)-4a − d, and (E,Z,Z)-7a,b are described. Trienes containing enal or enone dienophiles cyclize in excellent yield under mild conditions using substoichiometric amounts of MeAlCl2, in most cases with high levels of diastereoselectivity. The thermal IMDA reactions of 1a, 4a, and 7a require forcing conditions and proceed in low yield with reversed stereoselectivity in the cases of 1a and 4a.
Bibliography:Medline
NIH RePORTER
ISSN:1523-7060
1523-7052
DOI:10.1021/ol015667k