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Katsukiyo Miura - One of the best experts on this subject based on the ideXlab platform.
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diisobutylaluminum hydride promoted cyclization of o trimethylsilylethynyl styrenes to substituted naphthalenes
Tetrahedron Letters, 2016Co-Authors: Hidenori Kinoshita, Kazuki Yaguchi, Takayuki Tohjima, Nobuyoshi Hirai, Katsukiyo MiuraAbstract:Abstract The reaction of α,β-disubstituted ( E )- o -(trimethylsilylethynyl)styrenes with a substoichiometric amount of diisobutylaluminum hydride at 100 °C gave 1,2,3-trisubstituted naphthalenes. This benzocyclization is initiated by regioselective Hydroalumination of the alkyne moiety, and the resultant alkenylaluminums lead to naphthalenes through intramolecular carboalumination, skeletal rearrangement, and deHydroalumination steps. The silylated products could be efficiently transformed into iodinated polycyclic aromatic hydrocarbons.
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Hydroalumination-triggered cyclization of silylated 1,3-dien-5-ynes to polysubstituted benzenes.
Organic letters, 2014Co-Authors: Hidenori Kinoshita, Takayuki Tohjima, Katsukiyo MiuraAbstract:Regiocontrolled synthesis of polysubstituted benzenes from silylated 1,3-dien-5-ynes has been achieved by using diisobutylaluminum hydride (DIBAL-H). Hydroalumination of the alkyne moiety with DIBAL-H triggers the aromatic cyclization, which usually proceeds without rearrangement and loss of the existing substituents. The related unusual cyclizations to different types of polysubstituted benzenes are also described.
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Hydroalumination-Triggered Cyclization of Silylated 1,3-Dien-5-ynes to Polysubstituted Benzenes
2014Co-Authors: Hidenori Kinoshita, Takayuki Tohjima, Katsukiyo MiuraAbstract:Regiocontrolled synthesis of polysubstituted benzenes from silylated 1,3-dien-5-ynes has been achieved by using diisobutylaluminum hydride (DIBAL-H). Hydroalumination of the alkyne moiety with DIBAL-H triggers the aromatic cyclization, which usually proceeds without rearrangement and loss of the existing substituents. The related unusual cyclizations to different types of polysubstituted benzenes are also described
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Dialkylaluminum hydride-promoted cyclodimerization of silylated 1,3-enynes via skeletal rearrangement.
Organic letters, 2011Co-Authors: Hidenori Kinoshita, Tomoyuki Ishikawa, Katsukiyo MiuraAbstract:The dialkylaluminum hydride-promoted reaction of 1-silylalk-3-en-1-ynes gave symmetrical 1,2,3,5-tetrasubstituted benzenes as single regioisomers. The novel cyclodimerization via skeletal rearrangement can be rationalized by an unprecedented mechanism involving sequential Hydroalumination, alkene isomerization, carboalumination, carbon–carbon bond cleavage, and retro-Hydroalumination.
Keisuke Suzuki - One of the best experts on this subject based on the ideXlab platform.
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Stereogenic tert-alcohols via group-selective Hydroalumination: further scope
Tetrahedron Letters, 2002Co-Authors: Ken Ohmori, Yoshifumi Hachisu, Takao Suzuki, Keisuke SuzukiAbstract:Two classes of bis-alkynyl alcohols were subjected to Hydroalumination reaction, which, under suitable conditions, proceeded in a highly group-selective manner.
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Group-selective Hydroalumination: a novel route to stereogenic tert-alcohol centers.
Organic letters, 2001Co-Authors: Ken Ohmori, Takao Suzuki, Kimiko Taya, Daisuke Tanabe, Toshihiro Ohta, Keisuke SuzukiAbstract:A new group-selective reaction is described, that is, the Hydroalumination of bis-alkynyl alcohols armed with an adjacent stereogenic center, giving stereo-defined tert-alcohols of potential utility in natural product synthesis.
Ilan Marek - One of the best experts on this subject based on the ideXlab platform.
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Tandem Hydroalumination/Cu-Catalyzed Asymmetric Vinyl Metalation as a New Access to Enantioenriched Vinylcyclopropane Derivatives
Organic letters, 2017Co-Authors: Daniel S. Müller, Veronika Werner, Sema Akyol, Hans-günther Schmalz, Ilan MarekAbstract:Herein, we report the first enantio- and diastereoselective addition of stereodefined vinyl organometallic reagents to cyclopropenes. The operationally simple tandem Hydroalumination and copper-catalyzed vinylmetalation allows for the unique access of a diverse set of enantioenriched vinylcyclopropane derivatives.
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tandem Hydroalumination cu catalyzed asymmetric vinyl metalation as a new access to enantioenriched vinylcyclopropane derivatives
Organic Letters, 2017Co-Authors: Daniel S. Müller, Veronika Werner, Sema Akyol, Hans-günther Schmalz, Ilan MarekAbstract:Herein, we report the first enantio- and diastereoselective addition of stereodefined vinyl organometallic reagents to cyclopropenes. The operationally simple tandem Hydroalumination and copper-catalyzed vinylmetalation allows for the unique access of a diverse set of enantioenriched vinylcyclopropane derivatives.
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Tandem Hydroalumination/Cu-Catalyzed Asymmetric Vinyl Metalation as a New Access to Enantioenriched Vinylcyclopropane Derivatives
2017Co-Authors: Daniel S. Müller, Veronika Werner, Sema Akyol, Hans-günther Schmalz, Ilan MarekAbstract:Herein, we report the first enantio- and diastereoselective addition of stereodefined vinyl organometallic reagents to cyclopropenes. The operationally simple tandem Hydroalumination and copper-catalyzed vinylmetalation allows for the unique access of a diverse set of enantioenriched vinylcyclopropane derivatives
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Diastereoselective reduction of cyclopropenylcarbinol: new access to anti-cyclopropylcarbinol derivatives.
Organic letters, 2004Co-Authors: Elinor Zohar, Ilan MarekAbstract:[reaction: see text] Cyclopropenylcarbinol derivatives are regio- and diastereoselectively reduced with LiAlH(4) in Et(2)O into trans-cyclopropylcarbinols as a single isomer. The regioselectivity of the Hydroalumination reaction on the cyclopropenyl ring has been mapped out by deuterium labeling experiments.
Hidenori Kinoshita - One of the best experts on this subject based on the ideXlab platform.
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diisobutylaluminum hydride promoted cyclization of o trimethylsilylethynyl styrenes to substituted naphthalenes
Tetrahedron Letters, 2016Co-Authors: Hidenori Kinoshita, Kazuki Yaguchi, Takayuki Tohjima, Nobuyoshi Hirai, Katsukiyo MiuraAbstract:Abstract The reaction of α,β-disubstituted ( E )- o -(trimethylsilylethynyl)styrenes with a substoichiometric amount of diisobutylaluminum hydride at 100 °C gave 1,2,3-trisubstituted naphthalenes. This benzocyclization is initiated by regioselective Hydroalumination of the alkyne moiety, and the resultant alkenylaluminums lead to naphthalenes through intramolecular carboalumination, skeletal rearrangement, and deHydroalumination steps. The silylated products could be efficiently transformed into iodinated polycyclic aromatic hydrocarbons.
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Hydroalumination-triggered cyclization of silylated 1,3-dien-5-ynes to polysubstituted benzenes.
Organic letters, 2014Co-Authors: Hidenori Kinoshita, Takayuki Tohjima, Katsukiyo MiuraAbstract:Regiocontrolled synthesis of polysubstituted benzenes from silylated 1,3-dien-5-ynes has been achieved by using diisobutylaluminum hydride (DIBAL-H). Hydroalumination of the alkyne moiety with DIBAL-H triggers the aromatic cyclization, which usually proceeds without rearrangement and loss of the existing substituents. The related unusual cyclizations to different types of polysubstituted benzenes are also described.
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Hydroalumination-Triggered Cyclization of Silylated 1,3-Dien-5-ynes to Polysubstituted Benzenes
2014Co-Authors: Hidenori Kinoshita, Takayuki Tohjima, Katsukiyo MiuraAbstract:Regiocontrolled synthesis of polysubstituted benzenes from silylated 1,3-dien-5-ynes has been achieved by using diisobutylaluminum hydride (DIBAL-H). Hydroalumination of the alkyne moiety with DIBAL-H triggers the aromatic cyclization, which usually proceeds without rearrangement and loss of the existing substituents. The related unusual cyclizations to different types of polysubstituted benzenes are also described
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Dialkylaluminum hydride-promoted cyclodimerization of silylated 1,3-enynes via skeletal rearrangement.
Organic letters, 2011Co-Authors: Hidenori Kinoshita, Tomoyuki Ishikawa, Katsukiyo MiuraAbstract:The dialkylaluminum hydride-promoted reaction of 1-silylalk-3-en-1-ynes gave symmetrical 1,2,3,5-tetrasubstituted benzenes as single regioisomers. The novel cyclodimerization via skeletal rearrangement can be rationalized by an unprecedented mechanism involving sequential Hydroalumination, alkene isomerization, carboalumination, carbon–carbon bond cleavage, and retro-Hydroalumination.
Alexandre Alexakis - One of the best experts on this subject based on the ideXlab platform.
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New experimental conditions for tandem Hydroalumination/Cu-catalyzed asymmetric conjugate additions to β-substituted cyclic enones.
Organic letters, 2011Co-Authors: Daniel Müller, Matthieu Tissot, Alexandre AlexakisAbstract:Readily available alkenylalanes, arising from Hydroalumination of unprotected terminal alkynes, have been directly employed for the copper-catalyzed asymmetric conjugate addition (ACA) to β-substituted cyclic enones. The desired products, containing a quaternary stereogenic center, are generally obtained in good yields and enantioselectivities.
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new experimental conditions for tandem Hydroalumination cu catalyzed asymmetric conjugate additions to β substituted cyclic enones
Organic Letters, 2011Co-Authors: Daniel Müller, Matthieu Tissot, Alexandre AlexakisAbstract:Readily available alkenylalanes, arising from Hydroalumination of unprotected terminal alkynes, have been directly employed for the copper-catalyzed asymmetric conjugate addition (ACA) to β-substituted cyclic enones. The desired products, containing a quaternary stereogenic center, are generally obtained in good yields and enantioselectivities.