Why a proximity-induced Diels-Alder reaction is so fast

Krenske, Elizabeth H., Perry, Emma W., Jerome, Steven V., Maimone, Thomas J., Baran, Phil S. and Houk, K. N. (2012) Why a proximity-induced Diels-Alder reaction is so fast. Organic Letters, 14 12: 3016-3019. doi:10.1021/ol301083q

Author Krenske, Elizabeth H.
Perry, Emma W.
Jerome, Steven V.
Maimone, Thomas J.
Baran, Phil S.
Houk, K. N.
Title Why a proximity-induced Diels-Alder reaction is so fast
Journal name Organic Letters   Check publisher's open access policy
ISSN 1523-7060
Publication date 2012-06-15
Sub-type Article (original research)
DOI 10.1021/ol301083q
Volume 14
Issue 12
Start page 3016
End page 3019
Total pages 4
Place of publication Washington, DC, United States
Publisher American Chemical Society
Collection year 2013
Language eng
Abstract Unlike normal Diels–Alder reactions of acyclic alkadienes with alkenes, the vinylbicyclo[2.2.2]octene employed in the Baran total synthesis of vinigrol undergoes a quantitative Diels–Alder reaction with a tethered alkene at room temperature. Density functional theory calculations reveal that this unprecedented reactivity originates from a combination of preorganization, diene strain, and tether stabilization.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Non HERDC
School of Chemistry and Molecular Biosciences
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Citation counts: TR Web of Science Citation Count  Cited 17 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 18 times in Scopus Article | Citations
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Created: Mon, 11 Feb 2013, 14:46:58 EST by Elizabeth Krenske on behalf of School of Chemistry & Molecular Biosciences