Lewis acid catalyzed enlargement of cyclic β-alkoxyenals and one-pot synthesis of polyfunctional enoxysilanes derived from aucubin with trimethylsilyldiazomethane

Chemistry - A European Journal

Volumn 19, Issue 15, 2013, Pages 4686-4690

  Lemus, Christelle ^a   Poleschak, Marko ^a   Gailly, Sophie ^a   Desage El Murr, Marine ^a   Koch, Michel ^a   Deguin, Brigitte ^a  

^a FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

Author keywords

aldehydes; enals; homologation; Lewis acids; trimethylsilyldiazomethane

Indexed keywords

CARBONYL FUNCTION; ENALS; HOMOLOGATION; LEWIS ACID; ONE-POT SYNTHESIS; STEREO-SELECTIVE; TRIFLUOROMETHANESULFONATE; TRIMETHYLSILYLDIAZOMETHANE;

ALDEHYDES; CHEMISTRY; SYNTHESIS (CHEMICAL);

CATALYSTS;

ALDEHYDE; AUCUBIN; DIAZOMETHANE; DRUG DERIVATIVE; HYDROCARBON; IRIDOID; LEWIS ACID; TRIMETHYLSILYL DERIVATIVE; TRIMETHYLSILYLDIAZOMETHANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CATALYSIS; DIAZOMETHANE; HYDROCARBONS, CYCLIC; IRIDOID GLUCOSIDES; LEWIS ACIDS; MOLECULAR STRUCTURE; STEREOISOMERISM; TRIMETHYLSILYL COMPOUNDS;

EID: 84875873671     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203968     Document Type: Article

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36. Notably, the reaction leads to the preferential formation of (Z)- 6 isomers. Our results do not permit a clear explication of this observation and in silico studies are in process.