Imino-Diels–Alder and imino-aldol reactions catalyzed by samarium diiodide

In the presence of a catalytic amount of samarium diiodide in methylene chloride, aromatic imines react with Danishefsky diene to form tetrahydropyridine-4-ones in high yields. Under the same conditions, various imino-aldol reactions afford β-amino esters or β-amino ketones. Graphic

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Bibliographic Details
Published inTetrahedron letters Vol. 42; no. 42; pp. 7405 - 7407
Main Authors Collin, Jacqueline, Jaber, Nada, Lannou, Marie Isabelle
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.10.2001
Elsevier
Subjects
aldol reaction
Catalysis
Chemical Sciences
Chemistry
Chemistry, Organic
cycloadditions
imines
Organic chemistry
Physical Sciences
samarium diiodide
Science & Technology
aldol reaction
catalysis
imines
cycloadditions
samarium diiodide
ADDITION-REACTION
ALDEHYDES
TRIFLATE
KETENE SILYL ACETALS
EFFICIENT CATALYST
MANNICH-TYPE REACTION
COUPLING REACTIONS
QUINOLINE DERIVATIVES
ALDIMINE
3-COMPONENT
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Summary:In the presence of a catalytic amount of samarium diiodide in methylene chloride, aromatic imines react with Danishefsky diene to form tetrahydropyridine-4-ones in high yields. Under the same conditions, various imino-aldol reactions afford β-amino esters or β-amino ketones. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)01581-7