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 in:Organic letters 2003-10, Vol.5 (22), p.4069-4072
Main Authors: Forest, Jeremy, Bee, Cisco, Cordaro, Frank, Tius, Marcus A
Format: Article
Language:English
Subjects:
Cyclization
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Ethers - chemistry
Isomerism
Molecular Structure
Silica Gel
Silicon Dioxide - chemistry
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Description
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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035498z