Research Topics
| Ryo ShintaniSummaryAffiliation: Kyoto University Country: Japan Publications
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Publications
Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines via enantioselective transmetalationRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
J Am Chem Soc 134:16955-8. 2012..A rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines has been developed. High enantioselectivities have been achieved by employing (S,S)-Me-Duphos as the ligand through "enantioselective transmetalation"...- Palladium-catalyzed synthesis of 4-oxaspiro[2.4]heptanes via central attack of oxygen nucleophiles to π-allylpalladium intermediatesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Org Lett 14:2410-3. 2012..The course of the reaction is highly dependent on ligands and solvents, and selective formation of methylenetetrahydropyrans has also been realized... 
Palladium-catalyzed desymmetrization of silacyclobutanes with alkynes: enantioselective synthesis of silicon-stereogenic 1-sila-2-cyclohexenes and mechanistic considerationsRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Org Lett 14:2902-5. 2012....- Rhodium-catalyzed asymmetric 1,4-addition of sodium tetraarylborates to β,β-disubstituted α,β-unsaturated estersRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Org Lett 13:350-2. 2011..Highly efficient asymmetric catalysis has also been described to create quaternary carbon stereocenters at the β-position of esters by tuning the ester group of substrates and employing a readily available chiral diene ligand... - Palladium-catalyzed asymmetric synthesis of 2-pyrrolidinones with a quaternary carbon stereocenterRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Chem Commun (Camb) 48:9936-8. 2012..High enantioselectivity has been realized by employing a newly synthesized chiral phosphoramidite ligand... - Palladium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzosiloles via enantioselective C-H bond functionalizationRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
J Am Chem Soc 134:7305-8. 2012..High chemo- and enantioselectivities are achieved by employing a Josiphos-type ligand under mild conditions... - Rhodium-catalyzed asymmetric addition of potassium organotrifluoroborates to N-sulfonyl ketiminesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Org Lett 13:2977-9. 2011..High enantioselectivity has been achieved by using a chiral diene ligand, and the nosyl group of the addition products can be easily removed while retaining the enantiomeric purity... - Design and synthesis of new chiral phosphorus-olefin bidentate ligands and their use in the rhodium-catalyzed asymmetric addition of organoboroxines to N-sulfonyl iminesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Chem Commun (Camb) 47:6123-5. 2011..These ligands have been applied to a rhodium-catalyzed asymmetric addition of organoboroxines to N-sulfonyl aldimines, achieving high yield and enantioselectivity... - Synthesis of nine-membered azlactones by palladium-catalyzed ring-expansion of γ-methylidene-δ-valerolactones with aziridinesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, Japan
J Org Chem 76:4776-80. 2011..The products thus obtained can also be further functionalized with ease... - Palladium-catalyzed enantioselective desymmetrization of silacyclobutanes: construction of silacycles possessing a tetraorganosilicon stereocenterRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
J Am Chem Soc 133:16440-3. 2011.... - Rhodium-catalyzed asymmetric arylation of N-tosyl ketiminesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
J Am Chem Soc 132:13168-9. 2010..Highly efficient asymmetric catalysis has been achieved by employing a chiral diene ligand, constructing chiral amine derivatives possessing α-tetrasubstituted carbon stereocenters with high enantioselectivity... - Copper-catalyzed asymmetric addition of arylboronates to isatins: a catalytic cycle involving alkoxocopper intermediatesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Chem Commun (Camb) 46:6822-4. 2010..The catalytic cycle of this process has been examined through a series of stoichiometric reactions and an effective asymmetric variant has also been described by the use of a chiral N-heterocyclic carbene ligand... - Rhodium-catalyzed asymmetric arylation of azomethine iminesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Org Lett 12:4106-9. 2010..Highly efficient asymmetric catalysis has also been achieved by employing a chiral diene ligand to give 1-(diarylmethyl)pyrazolidin-3-ones with high enantioselectivity... - Guiding the nitrogen nucleophile to the middle: palladium-catalyzed decarboxylative cyclopropanation of 2-alkylidenetrimethylene carbonates with isocyanatesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Chem Commun (Camb) 47:3057-9. 2011..The site of nucleophilic attack is directed by connecting the two reaction components and by employing an electron-deficient triarylphosphine ligand... - Palladium-catalyzed intramolecular decarboxylative allylic arylation of alpha-aryl-gamma-methylidene-delta-valerolactonesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Chem Commun (Camb) 46:1697-9. 2010..The reaction can be conducted on a gram scale and the products thus obtained are further derivatized with ease... - Preparation of arylzinc reagents and their use in the rhodium-catalyzed asymmetric 1,4-addition for the synthesis of 2-aryl-4-piperidonesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Nat Protoc 2:2903-9. 2007..A detailed protocol is described using the preparation of 4-fluorophenylzinc chloride and its addition to benzyl 3,4-dihydro-4-oxo-1(2H)-pyridinecarboxylate in the presence of [RhCl((R)-binap)]2 as an example... - Palladium-catalyzed decarboxylative [4 + 3] cyclization of gamma-methylidene-delta-valerolactones with 1,1-dicyanocyclopropanesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Org Lett 11:5642-5. 2009..In addition, selective ring-expansion reactions can be achieved for certain gamma-methylidene-delta-valerolactones to give nondecarboxylated nine-membered lactones... - Stereoselective synthesis of spirooxindoles by palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatinsRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Org Lett 11:3754-6. 2009..Preliminary results of its application to asymmetric catalysis using a chiral phosphoramidite ligand are also described... - Stereoselective synthesis of nipecotic acid derivatives via palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with iminesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Org Lett 11:457-9. 2009..The products thus obtained can be further derivatized with high efficiency under simple reaction conditions... - Rhodium-catalyzed kinetic resolution of tertiary homoallyl alcohols via stereoselective carbon-carbon bond cleavageRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
Org Lett 10:1191-3. 2008..Selectivity factors of up to 12 have been achieved by employing (R)-H8-binap as the ligand, and the reaction can be conducted on a preparative scale... - Rhodium-catalyzed asymmetric synthesis of 3,3-disubstituted 1-indanonesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
Angew Chem Int Ed Engl 46:3735-7. 2007 - Chiral phosphine-olefin ligands in the rhodium-catalyzed asymmetric 1,4-addition reactionsWei Liang Duan
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
J Am Chem Soc 129:2130-8. 2007..A negative nonlinear effect derived from an inactive trimer-active monomer equilibrium of the catalyst was also successfully observed... - Rhodium-catalyzed asymmetric addition of arylboronic acids to beta-phthaliminoacrylate esters toward the synthesis of beta-amino acidsTakahiro Nishimura
Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606 8502, Japan
J Am Chem Soc 132:464-5. 2010.... - A new entry of nucleophiles in rhodium-catalyzed asymmetric 1,4-addition reactions: addition of organozinc reagents for the synthesis of 2-aryl-4-piperidonesRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
J Am Chem Soc 126:6240-1. 2004..While other conventional nucleophiles fail, organozinc reagents have been successfully utilized for the construction of these useful compounds in very good yield and enantiomeric excess... - Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatinsRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
Angew Chem Int Ed Engl 45:3353-6. 2006 - Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compoundsRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
Org Lett 6:3425-7. 2004..While phosphorus-based chiral ligands fail to induce high stereoselectivity, chiral norbornadiene ligands have proved to be uniquely effective to achieve high enantioselectivity in these 1,4-addition reactions... - Mechanistic Investigation of the Palladium-Catalyzed Decarboxylative Cyclization of gamma-Methylidene-delta-valerolactones with Isocyanates: Kinetic Studies and Origin of the Site Selectivity in the Nucleophilic Attack at a (pi-Allyl)palladiumRyo Shintani
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
J Am Chem Soc 132:7508-13. 2010..4]heptanones 4. These studies represent the first systematic investigation into the selectivity between terminal attack and central attack at (pi-allyl)palladium species by nitrogen-based nucleophiles... - Catalytic enantioselective synthesis of beta-lactams: intramolecular Kinugasa reactions and interception of an intermediate in the reaction cascadeRyo Shintani
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 42:4082-5. 2003 - A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocyclesRyo Shintani
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 125:10778-9. 2003..Through the use of a chiral phosphaferrocene-oxazoline ligand, a wide range of substrates can be coupled to generate useful heterocycles in very good enantiomeric excess...