A Complementary Process to Pauson–Khand-Type Annulation Reactions for the Construction of Fully Substituted Cyclopentenones

A complementary process to the Pauson–Khand annulation is described that is well suited to forging densely substituted/oxygenated cyclopentenone products (including fully substituted variants). The reaction is thought to proceed through a sequence of metallacycle-mediated bond-forming events that en...

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Bibliographic Details
Published in:Organic letters 2019-01, Vol.21 (2), p.567-570
Main Authors: Millham, Adam B, Kier, Matthew J, Leon, Robert M, Karmakar, Rajdip, Stempel, Zachary D, Micalizio, Glenn C
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Molecular Structure
Oxygen - chemistry
Propanols - chemistry
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Summary:A complementary process to the Pauson–Khand annulation is described that is well suited to forging densely substituted/oxygenated cyclopentenone products (including fully substituted variants). The reaction is thought to proceed through a sequence of metallacycle-mediated bond-forming events that engages an internal alkyne and a β-keto ester in an annulation process that forges two C–C bonds. A variant of this annulation process has also been established that delivers deoxygenated cyclopentenones that lack the allylic tertiary alcohol.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03922