A Facile Synthesis of α-Phenylchalcogeno(S, Se) α,β-Unsaturated Esters from Ethyl α-Bromo-α-phenylchalcogeno Acetates

Ethyl α-bromo-α-phenylseleno acetate 1 and ethyl α-bromo-α-phenylthio acetate 2 react with aldehydes in the presence of dibutyltelluride to give α-phenylchalcogeno-α,β-unsaturated esters, with Z preferential stereochemistry.

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Bibliographic Details
Published inSynthetic communications Vol. 28; no. 18; pp. 3371 - 3380
Main Authors Silveira, C. C., Botega, C. S., Rhoden, C. R. B., Nunes, M. R. S., Braga, A. L., Lenardão, E. J.
Format Journal Article
LanguageEnglish
Published NEW YORK Taylor & Francis Group 01.09.1998
Marcel Dekker Inc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
STABILIZED TELLURONIUM YLIDES
WITTIG-TYPE REACTION
DIFFERENT STRONG BASES
ORGANIC-SYNTHESIS
CARBONYL-COMPOUNDS
HIGHLY STEREOSELECTIVE SYNTHESIS
ORGANOLITHIUM REAGENTS
CYCLOPROPANATION REACTIONS
TELLURIUM REAGENTS
GAMMA-BUTYROLACTONES
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Summary:Ethyl α-bromo-α-phenylseleno acetate 1 and ethyl α-bromo-α-phenylthio acetate 2 react with aldehydes in the presence of dibutyltelluride to give α-phenylchalcogeno-α,β-unsaturated esters, with Z preferential stereochemistry.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397919808004444