Lewis Acid Catalyzed Enlargement of Cyclic β-Alkoxyenals and One-Pot Synthesis of Polyfunctional Enoxysilanes Derived from Aucubin with Trimethylsilyldiazomethane

Pyrane to oxepane in one step: Highly regio‐ and stereoselective homologations dependent on the nature of carbonyl function and catalysts have been observed during the formation of enoxysilanes (see scheme). Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and AlCl3 were identified as suitable cata...

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Bibliographic Details
Published in:Chemistry : a European journal 2013-04, Vol.19 (15), p.4686-4690
Main Authors: Lemus, Christelle, Poleschak, Marko, Gailly, Sophie, Desage-El Murr, Marine, Koch, Michel, Deguin, Brigitte
Format: Article
Language:English
Subjects:
aldehydes
Aldehydes - chemistry
Catalysis
Diazomethane - analogs & derivatives
Diazomethane - chemical synthesis
Diazomethane - chemistry
enals
homologation
Hydrocarbons, Cyclic - chemistry
Iridoid Glucosides - chemical synthesis
Iridoid Glucosides - chemistry
Lewis acids
Lewis Acids - chemistry
Molecular Structure
Stereoisomerism
Trimethylsilyl Compounds - chemical synthesis
Trimethylsilyl Compounds - chemistry
trimethylsilyldiazomethane
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Summary:Pyrane to oxepane in one step: Highly regio‐ and stereoselective homologations dependent on the nature of carbonyl function and catalysts have been observed during the formation of enoxysilanes (see scheme). Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and AlCl3 were identified as suitable catalysts to promote the homologation and ring‐enlargement.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201203968