Gold-Catalyzed Cycloisomerization of 1,5-Allenynes via Dual Activation of an Ene Reaction

Gold-Catalyzed Cycloisomerization of 1,5-Allenynes via Dual Activation of an Ene Reaction

Tris(triphenylphosphinegold) oxonium tetrafluoroborate, [(Ph3PAu)3O]BF4, catalyzes the rearrangement of 1,5-allenynes to produce cross-conjugated trienes. Experimental and computational evidence shows that the ene reaction proceeds through a unique nucleophilic addition of an allene double bond to a...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 130; no. 13; pp. 4517 - 4526
Main Authors: Cheong, Paul Ha-Yeon, Morganelli, Philip, Luzung, Michael R, Houk, K. N, Toste, F. Dean
Format: Journal Article
Language:English
Published: United States American Chemical Society 02-04-2008
Subjects:
Alkadienes - chemical synthesis
Alkadienes - chemistry
Alkynes - chemistry
Catalysis
Cyclization
Models, Chemical
Molecular Structure
Organogold Compounds - chemistry
Stereoisomerism
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Summary:Tris(triphenylphosphinegold) oxonium tetrafluoroborate, [(Ph3PAu)3O]BF4, catalyzes the rearrangement of 1,5-allenynes to produce cross-conjugated trienes. Experimental and computational evidence shows that the ene reaction proceeds through a unique nucleophilic addition of an allene double bond to a cationic phosphinegold(I)-complexed phosphinegold(I) acetylide, followed by a 1,5-hydrogen shift.
Bibliography:istex:B84F8C2BA269999D91A2AFD80C8F99E2022FA115
ark:/67375/TPS-BC2GR3QH-D
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja711058f