BIOMAT Database Logo BIOMAT Database Logo

Gold-catalyzed hydroamination/cycloisomerization reaction of 1,6-enynes. 2007

Lucie Leseurre, and Patrick Yves Toullec, and Jean-Pierre Genêt, and Véronique Michelet
Laboratoire de Synthèse Sélective Organique et Produits Naturels, E.N.S.C.P., UMR 7573, 11 rue P. et M. Curie, F-75231 Paris Cedex 05, France.

An efficient Au(I) catalytic system is described for the hydroamination/cycloisomerization reaction of functionalized 1,6-enynes. The reaction leads to carbo- and heterocyclic amino derivatives in good to excellent yields. The cyclizations were conducted in the presence of PPh(3)AuCl/AgSbF(6) catalyst in THF or dioxane at room temperature. The use of allyloxycarbonyl carbamate has allowed the formation of free amino derivatives via sequential Au- and Pd-catalyzed reactions.

UI MeSH Term Description Entries
D007536 Isomerism The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Isomerisms
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D006046 Gold A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.
D006859 Hydrogen The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas. Protium,Hydrogen-1
D000586 Amination The creation of an amine. It can be produced by the addition of an amino group to an organic compound or reduction of a nitro group. Aminations
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

Related Publications

Lucie Leseurre, and Patrick Yves Toullec, and Jean-Pierre Genêt, and Véronique Michelet
Iridium complex-catalyzed reaction of 1,6-enynes: cycloaddition and cycloisomerization.
April 2005, Organic letters,
Lucie Leseurre, and Patrick Yves Toullec, and Jean-Pierre Genêt, and Véronique Michelet
Gold(I)-Catalyzed Cycloisomerization-Dimerization Cascade of Benzene-Tethered 1,6-Enynes.
July 2017, The Journal of organic chemistry,
Lucie Leseurre, and Patrick Yves Toullec, and Jean-Pierre Genêt, and Véronique Michelet
Rh(I)-Catalyzed Cycloisomerization of 1,6-Enynes.
July 2015, Synlett : accounts and rapid communications in synthetic organic chemistry,
Lucie Leseurre, and Patrick Yves Toullec, and Jean-Pierre Genêt, and Véronique Michelet
Enantioselective Rhodium-Catalyzed Cycloisomerization of (E)-1,6-Enynes.
May 2016, Angewandte Chemie (International ed. in English),
Lucie Leseurre, and Patrick Yves Toullec, and Jean-Pierre Genêt, and Véronique Michelet
Gold(I)-catalyzed cycloisomerization of enynes containing cyclopropenes.
August 2010, Angewandte Chemie (International ed. in English),
Lucie Leseurre, and Patrick Yves Toullec, and Jean-Pierre Genêt, and Véronique Michelet
Gold-catalyzed cycloisomerization of siloxy enynes to cyclohexadienes.
September 2004, Journal of the American Chemical Society,
Lucie Leseurre, and Patrick Yves Toullec, and Jean-Pierre Genêt, and Véronique Michelet
Gold(i)-catalyzed dehydrogenative cycloisomerization of 1,5-enynes.
September 2016, Chemical communications (Cambridge, England),
Lucie Leseurre, and Patrick Yves Toullec, and Jean-Pierre Genêt, and Véronique Michelet
Cobalt-catalyzed cycloisomerization of 1,6-enynes and allyl propargyl ethers.
July 2003, Organic letters,
Lucie Leseurre, and Patrick Yves Toullec, and Jean-Pierre Genêt, and Véronique Michelet
Rhodium-catalyzed cycloisomerization of 1,6-enynes with an intramolecular halogen shift: reaction scope and mechanism.
June 2004, Journal of the American Chemical Society,
Lucie Leseurre, and Patrick Yves Toullec, and Jean-Pierre Genêt, and Véronique Michelet
Gold(I)-catalyzed cycloisomerization of 3-methoxy-1,6-enynes featuring tandem cyclization and [3,3]-sigmatropic rearrangement.
January 2008, Angewandte Chemie (International ed. in English),
Copied contents to your clipboard!