Isomerization−Cyclization Approach to the Synthesis of 2-Hydroxy-5-alkylidene-cyclopent-2-enones

Propargyl vinyl ketones that are derived from the addition of 1-lithio-1-methoxymethoxy-2-ynes to morpholino enamides undergo isomerization followed by cyclization to α-methylene cyclopentenones upon exposure to silica gel.

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Bibliographic Details
Published inOrganic letters Vol. 5; no. 22; pp. 4069 - 4072
Main Authors Forest, Jeremy, Bee, Cisco, Cordaro, Frank, Tius, Marcus A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 30.10.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cyclization
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Ethers - chemistry
Isomerism
Molecular Structure
Physical Sciences
Science & Technology
Silica Gel
Silicon Dioxide - chemistry
ESTER
ETHERS
CYCLOPENTANNELATION
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Summary:Propargyl vinyl ketones that are derived from the addition of 1-lithio-1-methoxymethoxy-2-ynes to morpholino enamides undergo isomerization followed by cyclization to α-methylene cyclopentenones upon exposure to silica gel.
Bibliography:Medline
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035498z