Hydroalumination of seleno acetylenes: a versatile generation and reactions of alpha-aluminate vinyl selenide intermediates in the highly regio and stereoselective synthesis of telluro(seleno)ketene acetals

The hydroalumination of butylseleno acetylenes with DIBAL-H followed by addition of n-butyllithium generated in situ the (Z)-butylseleno vinyl alanates intermediates which were captured with C4H9TeBr furnishing the (E)-telluro(seleno)ketene acetals exclusively. The isomers with opposite stereochemis...

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Bibliographic Details
Published inTetrahedron letters Vol. 49; no. 24; pp. 3872 - 3876
Main Authors Guerrero, Palimclo G., Dabdoub, Miguel J., Baroni, Adriano C. M.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 09.06.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHALCOGENIDES
CROSS-COUPLING REACTIONS
ORGANOTELLURIUM COMPOUNDS
HYDROZIRCONATION
EXCHANGE
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Summary:The hydroalumination of butylseleno acetylenes with DIBAL-H followed by addition of n-butyllithium generated in situ the (Z)-butylseleno vinyl alanates intermediates which were captured with C4H9TeBr furnishing the (E)-telluro(seleno)ketene acetals exclusively. The isomers with opposite stereochemistry (Z)-telluro(seleno)ketene acetals were obtained by the reduction of phenylseleno acetylenes with lithium di-(isobutyl)-n-butyl aluminate hydride (Zweifel's reagent) followed by reaction of (E)-phenylseleno vinyl alanates intermediates with C4H9TeBr. (c) 2008 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2008.04.072