Thiazolinium salt: an efficient catalyst for the Mukaiyama reaction

Mukaiyama aldol reaction between benzaldehyde and Danishefsky diene is promoted by ionic liquid-type salts. Hence, thiazolinium salts have been found to be the most efficient for this transformation. On a mechanistic point of view, only the Mukaiyama process is observed without any hetero Diels–Alde...

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Published inTetrahedron letters Vol. 50; no. 52; pp. 7239 - 7241
Main Authors Mercey, Guillaume, Brégeon, Delphine, Baudequin, Christine, Guillen, Frédéric, Levillain, Jocelyne, Gulea, Mihaela, Plaquevent, Jean-Christophe, Gaumont, Annie-Claude
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.12.2009
Elsevier
Subjects
Chemical Sciences
Dihydropyranones
Ionic liquids
Mukaiyama reaction
Organic chemistry
Thiazolinium salt
Ionic liquids
Mukaiyama reaction
Thiazolinium salt
Dihydropyranones
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Summary:Mukaiyama aldol reaction between benzaldehyde and Danishefsky diene is promoted by ionic liquid-type salts. Hence, thiazolinium salts have been found to be the most efficient for this transformation. On a mechanistic point of view, only the Mukaiyama process is observed without any hetero Diels–Alder cycloaddition. In some cases, cyclisation of the Mukaiyama adduct occurred without addition of TFA. Interestingly, the thiazolinium catalyst can be recycled at least 10 times without loss of activity.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.09.168