Use of metalated enecarbamates in the squarate cascade. Direct access to highly functionalized 2,4-cyclooctadienones by intramolecular interception of the mesocyclic dienolates

Leo A. Paquette; Jingsung Tae

doi:10.1016/S0040-4039(97)00565-0

Use of metalated enecarbamates in the squarate cascade. Direct access to highly functionalized 2,4-cyclooctadienones by intramolecular interception of the mesocyclic dienolates

Leo A. Paquette, Jingsung Tae

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

25 Citations (Scopus)

Abstract

A new method for constructing highly functionalized eight-membered ring ketones, fused to one or two additional rings as desired, is reported.

Original language	English
Pages (from-to)	3151-3154
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4039(97)00565-0
Publication status	Published - 1997 May 5

Bibliographical note

Funding Information:
17 O 18 19 hetero atoms are bonded to the same cyclopentene. This interesting chemical transposition is made possible because the release of enolate anion 17 triggers transannular aldolization and generation of 18. In turn, the proximity factors that now develop allow for reintroduction of a cyclic carbamate moiety. Acknowledgment. The financial support of the National Science Foundation is gratefully acknowledged. X-ray crystallographic results were recorded by Prof. Robin Rogers and Dr. Judith Gallucci whom we thank.

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "A new method for constructing highly functionalized eight-membered ring ketones, fused to one or two additional rings as desired, is reported.",

author = "Paquette, {Leo A.} and Jingsung Tae",

note = "Funding Information: 17 O 18 19 hetero atoms are bonded to the same cyclopentene. This interesting chemical transposition is made possible because the release of enolate anion 17 triggers transannular aldolization and generation of 18. In turn, the proximity factors that now develop allow for reintroduction of a cyclic carbamate moiety. Acknowledgment. The financial support of the National Science Foundation is gratefully acknowledged. X-ray crystallographic results were recorded by Prof. Robin Rogers and Dr. Judith Gallucci whom we thank.",

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AU - Paquette, Leo A.

AU - Tae, Jingsung

N1 - Funding Information: 17 O 18 19 hetero atoms are bonded to the same cyclopentene. This interesting chemical transposition is made possible because the release of enolate anion 17 triggers transannular aldolization and generation of 18. In turn, the proximity factors that now develop allow for reintroduction of a cyclic carbamate moiety. Acknowledgment. The financial support of the National Science Foundation is gratefully acknowledged. X-ray crystallographic results were recorded by Prof. Robin Rogers and Dr. Judith Gallucci whom we thank.

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N2 - A new method for constructing highly functionalized eight-membered ring ketones, fused to one or two additional rings as desired, is reported.

AB - A new method for constructing highly functionalized eight-membered ring ketones, fused to one or two additional rings as desired, is reported.

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Use of metalated enecarbamates in the squarate cascade. Direct access to highly functionalized 2,4-cyclooctadienones by intramolecular interception of the mesocyclic dienolates

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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