Antimony pentachloride catalyzed Diels–Alder reactions: improved regioselectivity in the synthesis of dialkyl naphthoquinones

Improved regioselectivity in catalyzed Diels–Alder (DA) cycloadditions between non-symmetrical benzoquinones and mono-substituted butadienes is achieved by use of SbCl 5. After oxidation, good yields of dialkylnaphthoquinones are obtained. The greater steric demand in comparison to other Lewis acids...

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Bibliographic Details
Published inTetrahedron letters Vol. 42; no. 2; pp. 219 - 221
Main Authors Nunes, Ruth Leandro, Bieber, Lothar Wilhelm
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.01.2001
Elsevier
Subjects
antimony pentachloride
benzoquinones
Chemistry
Chemistry, Organic
Diels–Alder reactions
Physical Sciences
regioselectivity
Science & Technology
regioselectivity
Diels–Alder reactions
benzoquinones
antimony pentachloride
Diels-Alder reactions
LEWIS ACID
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Summary:Improved regioselectivity in catalyzed Diels–Alder (DA) cycloadditions between non-symmetrical benzoquinones and mono-substituted butadienes is achieved by use of SbCl 5. After oxidation, good yields of dialkylnaphthoquinones are obtained. The greater steric demand in comparison to other Lewis acids (LAs) seems to favor the less hindered transition state. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)01968-7