Micellar catalysis enables copper-catalyzed silylcupration of a variety of electron-deficient alkynes, thereby providing access to isomerically pure E- or Z-β-silyl-substituted carbonyl derivatives. These reactions take place in minutes, afford high yields and stereoselectivity, and are especially tolerant of functional groups present in the substrates. The aqueous reaction medium has been successfully recycled several times, and a substrate/catalyst ratio of 10,000:1 has been documented for this methodology.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.201311035 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Stereoselective silylcupration of conjugated alkynes in water at room temperature.
Angew Chem Int Ed Engl
April 2014
Department of Chemistry & Biochemistry, University of California, Santa Barbara, CA 93106 (USA).
Micellar catalysis enables copper-catalyzed silylcupration of a variety of electron-deficient alkynes, thereby providing access to isomerically pure E- or Z-β-silyl-substituted carbonyl derivatives. These reactions take place in minutes, afford high yields and stereoselectivity, and are especially tolerant of functional groups present in the substrates. The aqueous reaction medium has been successfully recycled several times, and a substrate/catalyst ratio of 10,000:1 has been documented for this methodology.
View Article and Find Full Text PDFCuI/Pd0 cooperative dual catalysis: tunable stereoselective construction of tetra-substituted alkenes.
Chemistry
February 2014
Institute of Condensed Matter and Nanosciences-Molecules, Solids and Reactivity (IMCN/MOST), Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.03, 1348 Louvain-la-Neuve (Belgium), Fax: (+32) 10 47-41-68.
This paper describes a tunable and stereoselective dual catalytic system that uses copper and palladium reagents. This cooperative silylcupration and palladium-catalyzed allylation readily affords trisubstituted alkenylsilanes. Fine-tuning the reaction conditions allows selective access to one stereoisomer over the other.
View Article and Find Full Text PDFSeven-membered ring formation from cyclopropanated oxo- and epoxyallylsilanes.
J Org Chem
July 2011
Departamento de Química Orgánica, Universidad de Valladolid, Valladolid, Spain.
A useful strategy for cycloheptane annulations from oxo- and epoxyallylsilanes, prepared by silylcupration of allenes, has been developed, and their application to the stereoselective synthesis of 4-methylenecycloheptan-1-ols is of great potential in the construction of seven-membered ring natural products presented.
View Article and Find Full Text PDFSpiro-cyclopropanation from oxoallylsilanes.
J Am Chem Soc
June 2005
Departamento de Química Orgánica, Universidad de Valladolid, 47011 Valladolid, Spain.
A novel highly stereoselective spiro-cyclopropanation reaction from oxoallylsilanes is described. Oxoallylsilanes are readily obtained by silylcupration of allene followed by conjugate addition to enones. The former oxoallylsilanes undergo a tandem cyclization-cyclopropanation reaction when treated with CH2I2/Me3Al, leading to hydroxylated polycyclic systems bearing the spiro-cyclopropane moiety.
View Article and Find Full Text PDFStereocontrol in organic synthesis using silicon-containing compounds. Studies directed towards the synthesis of ebelactone A.
Org Biomol Chem
April 2004
Department of Chemistry, Lensfield Road, Cambridge, UK CB2 1EW.
Several approaches to the synthesis of ebelactone A 2 are described, culminating in the synthesis of the benzenesulfonate of 2-epi-ebelactone A 161. All the approaches were based on three fragments A, B and C, originally defined in general terms in, but eventually used as the aldehyde 72, the allenylsilane 3 and the aldehyde 139, respectively. They were joined, first B with C, and then B+C with A.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!