Hydroxyl-Directed Cyclizations of 1,6-Enynes

The palladium-catalyzed, hydroxyl-directed cyclization reactions of 1,6-enynes provide a highly diastereoselective process for the syntheses of stereochemically defined cyclopentanes. Consistently high levels of cis-selectivity are possible using homopropargyl alcohols in contrast to the correspondi...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 6; pp. 1517 - 1519
Main Authors Camelio, Andrew M, Barton, Thomas, Guo, Fenghai, Shaw, Travis, Siegel, Dionicio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.03.2011
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Cyclobutanes - chemistry
Heterocyclic Compounds, 2-Ring - chemical synthesis
Heterocyclic Compounds, 2-Ring - chemistry
Molecular Structure
Nitrogen Oxides - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
CYCLOISOMERIZATIONS
HOMOALLYL ALCOHOLS
RETRO-ALLYLATION
ARYL HALIDES
STOLONIDIOL
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Summary:The palladium-catalyzed, hydroxyl-directed cyclization reactions of 1,6-enynes provide a highly diastereoselective process for the syntheses of stereochemically defined cyclopentanes. Consistently high levels of cis-selectivity are possible using homopropargyl alcohols in contrast to the corresponding propargyl alcohols. Hydroborylative enyne cyclizations coupled with this directing group effect provide a useful method for the syntheses of multifaceted compounds bearing all carbon quaternary centers.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol200157x