Lewis acid-promoted generation of α-oxy- o-quinodimethanes and cycloaddition reactions

Treatment of stannyl aldehydes 5a, 5 b, and ketone 5c with MgBr 2 as the Lewis acid catalyst can initiate the internal cleavage reactions of carbon-tin σ bond leading to α-oxy-o-quinodimethanes, which can then undergo Diels - Alder cycloadditions. Anhydrous magnesium bromide can effectively promote...

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Bibliographic Details
Published inTetrahedron letters Vol. 35; no. 23; pp. 3975 - 3978
Main Author Hyung Woo, Soon
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.06.1994
Elsevier
Subjects
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
TETRAALKYLSTANNANES
CHEMISTRY
COMPLEX
CYCLIZATION
Lewis acid
Hydroxyester
Magnesium Bromides
Diels Alder addition
Acid catalysis
Aldehyde
Ketone
Naphthalene derivatives
Scission
Bicyclic compound
Aromatic compound
Quinonemethide
Organic stannane
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Summary:Treatment of stannyl aldehydes 5a, 5 b, and ketone 5c with MgBr 2 as the Lewis acid catalyst can initiate the internal cleavage reactions of carbon-tin σ bond leading to α-oxy-o-quinodimethanes, which can then undergo Diels - Alder cycloadditions. Anhydrous magnesium bromide can effectively promote to conversion of 5 to α- oxy -o -quinodimethanes 7, which can then undergo Diels-Alder cycloaddition reactions.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)76717-7