Four Nucleophilic Additions to Alkenynedioic Acid Derivatives in Tandem; Efficient One-Pot Synthesis of Bicyclo[4.2.0]octenols

When alkenynedioic acid derivatives were treated with a Grignard reagent, tandem cyclization and the incorporation of two molecules of the Grignard reagent occurred to give stereodefined bicyclo[4.2.0]octenols via four nucleophilic additions.

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 10; pp. 2450 - 2453
Main Authors Hata, Takeshi, Imade, Haduki, Urabe, Hirokazu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.05.2012
Amer Chemical Soc
Subjects
Alkenes - chemistry
Alkynes - chemistry
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Indicators and Reagents
Molecular Structure
Octanols - chemical synthesis
Octanols - chemistry
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
MULTICOMPONENT REACTIONS
METALATIVE CYCLIZATION
NATURAL-PRODUCT SYNTHESIS
ASYMMETRIC-SYNTHESIS
ORGANOCATALYTIC DOMINO REACTIONS
STEREOSELECTIVE-SYNTHESIS
MICHAEL-ALDOL REACTION
TRANSFORMATIONS
STRATEGIES
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Summary:When alkenynedioic acid derivatives were treated with a Grignard reagent, tandem cyclization and the incorporation of two molecules of the Grignard reagent occurred to give stereodefined bicyclo[4.2.0]octenols via four nucleophilic additions.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300623j