Intramolecular Diels−Alder Reactions of Siloxacyclopentene Constrained Trienes

The synthesis of siloxacyclopentene-constrained trienes 7 and 10 and studies of their IMDA cycloadditions are described. The use of appropriately chosen thermal or Lewis acid conditions allows for cycloadducts 3−6 to be obtained with high levels of diastereoselectivity. These adducts possess trans-r...

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 11; pp. 2243 - 2246
Main Authors Halvorsen, Geoff T, Roush, William R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.05.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cyclopentanes - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Siloxanes - chemistry
BOTTOM-HALF
POSTULATED BIOGENESIS
CROSS-METATHESIS
FR182877
ANTIMITOTIC SUBSTANCE
ENANTIOSELECTIVE SYNTHESIS
STEREOCHEMICAL ASPECTS
DIRECTING GROUP STRATEGY
OLEFIN METATHESIS
CHLOROTHRICOLIDE
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Summary:The synthesis of siloxacyclopentene-constrained trienes 7 and 10 and studies of their IMDA cycloadditions are described. The use of appropriately chosen thermal or Lewis acid conditions allows for cycloadducts 3−6 to be obtained with high levels of diastereoselectivity. These adducts possess trans-relationships between the hydroxyl group and the adjacent ring fusion proton, a stereochemical relationship not previously attainable in IMDA reactions.
Bibliography:Medline
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol070858u