Ryo Shintani

Summary

Affiliation: Kyoto University
Country: Japan

Publications

  1. doi request reprint Sodium tetraarylborates as effective nucleophiles in rhodium/diene-catalyzed 1,4-addition to beta,beta-disubstituted alpha,beta-unsaturated ketones: catalytic asymmetric construction of quaternary carbon stereocenters
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Am Chem Soc 131:13588-9. 2009
  2. ncbi request reprint Palladium-catalyzed synthesis of spiro[2.4]heptanes: ligand-dependent position control in the nucleophilic attack to a pi-allylpalladium intermediate
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Am Chem Soc 129:14866-7. 2007
  3. ncbi request reprint Catalytic asymmetric synthesis of allylsilanes through rhodium/chiral diene-catalyzed 1,4-addition of alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    Org Lett 9:4643-5. 2007
  4. doi request reprint Tuning the chiral environment of C2-symmetric diene ligands: development of 3,7-disubstituted bicyclo[3.3.1]nona-2,6-dienes
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Org Chem 74:869-73. 2009
  5. doi request reprint Palladium-catalyzed asymmetric decarboxylative lactamization of gamma-methylidene-delta-valerolactones with isocyanates: conversion of racemic lactones to enantioenriched lactams
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Am Chem Soc 130:16174-5. 2008
  6. ncbi request reprint Rhodium-catalyzed multicomponent-coupling reactions involving a carborhodation-cross-coupling sequence
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    Org Lett 8:4799-801. 2006
  7. doi request reprint 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)palladium
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Am Chem Soc 132:7508-13. 2010
  8. doi request reprint Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines via enantioselective transmetalation
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Am Chem Soc 134:16955-8. 2012
  9. doi request reprint Palladium-catalyzed synthesis of 4-oxaspiro[2.4]heptanes via central attack of oxygen nucleophiles to π-allylpalladium intermediates
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    Org Lett 14:2410-3. 2012
  10. doi request reprint Palladium-catalyzed desymmetrization of silacyclobutanes with alkynes: enantioselective synthesis of silicon-stereogenic 1-sila-2-cyclohexenes and mechanistic considerations
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    Org Lett 14:2902-5. 2012

Collaborators

Detail Information

Publications38

  1. doi request reprint Sodium tetraarylborates as effective nucleophiles in rhodium/diene-catalyzed 1,4-addition to beta,beta-disubstituted alpha,beta-unsaturated ketones: catalytic asymmetric construction of quaternary carbon stereocenters
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Am Chem Soc 131:13588-9. 2009
    ..Highly efficient asymmetric catalysis has also been achieved by employing a readily available chiral diene ligand, leading to the construction of quaternary carbon stereocenters with high enantioselectivity...
  2. ncbi request reprint Palladium-catalyzed synthesis of spiro[2.4]heptanes: ligand-dependent position control in the nucleophilic attack to a pi-allylpalladium intermediate
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Am Chem Soc 129:14866-7. 2007
    ..It was found that the course of the reaction is dependent on the ligand employed, and selective [4 + 2] cycloadditions can also be achieved by the use of a bulky monophosphine ligand...
  3. ncbi request reprint Catalytic asymmetric synthesis of allylsilanes through rhodium/chiral diene-catalyzed 1,4-addition of alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    Org Lett 9:4643-5. 2007
    ..The resulting allylsilanes can be used for stereoselective intramolecular allylation reactions to control two contiguous tertiary and quaternary stereocenters...
  4. doi request reprint Tuning the chiral environment of C2-symmetric diene ligands: development of 3,7-disubstituted bicyclo[3.3.1]nona-2,6-dienes
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Org Chem 74:869-73. 2009
    ....
  5. doi request reprint Palladium-catalyzed asymmetric decarboxylative lactamization of gamma-methylidene-delta-valerolactones with isocyanates: conversion of racemic lactones to enantioenriched lactams
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Am Chem Soc 130:16174-5. 2008
    ..High enantioselectivity has been achieved by tuning the ester group on substrate and the substituents of phosphoramidite ligand...
  6. ncbi request reprint Rhodium-catalyzed multicomponent-coupling reactions involving a carborhodation-cross-coupling sequence
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    Org Lett 8:4799-801. 2006
    ....
  7. doi request reprint 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)palladium
    Ryo 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...
  8. doi request reprint Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines via enantioselective transmetalation
    Ryo 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"...
  9. doi request reprint Palladium-catalyzed synthesis of 4-oxaspiro[2.4]heptanes via central attack of oxygen nucleophiles to π-allylpalladium intermediates
    Ryo 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...
  10. doi request reprint Palladium-catalyzed desymmetrization of silacyclobutanes with alkynes: enantioselective synthesis of silicon-stereogenic 1-sila-2-cyclohexenes and mechanistic considerations
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    Org Lett 14:2902-5. 2012
    ....
  11. doi request reprint Rhodium-catalyzed asymmetric 1,4-addition of sodium tetraarylborates to β,β-disubstituted α,β-unsaturated esters
    Ryo 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...
  12. doi request reprint Palladium-catalyzed asymmetric synthesis of 2-pyrrolidinones with a quaternary carbon stereocenter
    Ryo 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...
  13. doi request reprint Palladium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzosiloles via enantioselective C-H bond functionalization
    Ryo 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...
  14. doi request reprint Rhodium-catalyzed kinetic resolution of tertiary homoallyl alcohols via stereoselective carbon-carbon bond cleavage
    Ryo 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...
  15. doi request reprint Copper-catalyzed asymmetric addition of arylboronates to isatins: a catalytic cycle involving alkoxocopper intermediates
    Ryo 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...
  16. doi request reprint Rhodium-catalyzed asymmetric arylation of N-tosyl ketimines
    Ryo 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...
  17. doi request reprint Guiding the nitrogen nucleophile to the middle: palladium-catalyzed decarboxylative cyclopropanation of 2-alkylidenetrimethylene carbonates with isocyanates
    Ryo 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...
  18. doi request reprint Synthesis of nine-membered azlactones by palladium-catalyzed ring-expansion of γ-methylidene-δ-valerolactones with aziridines
    Ryo 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...
  19. doi request reprint Design and synthesis of new chiral phosphorus-olefin bidentate ligands and their use in the rhodium-catalyzed asymmetric addition of organoboroxines to N-sulfonyl imines
    Ryo 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...
  20. doi request reprint Rhodium-catalyzed asymmetric addition of potassium organotrifluoroborates to N-sulfonyl ketimines
    Ryo 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...
  21. doi request reprint Palladium-catalyzed enantioselective desymmetrization of silacyclobutanes: construction of silacycles possessing a tetraorganosilicon stereocenter
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Am Chem Soc 133:16440-3. 2011
    ....
  22. doi request reprint Rhodium-catalyzed asymmetric arylation of azomethine imines
    Ryo 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...
  23. doi request reprint Stereoselective synthesis of spirooxindoles by palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins
    Ryo 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...
  24. doi request reprint Palladium-catalyzed intramolecular decarboxylative allylic arylation of alpha-aryl-gamma-methylidene-delta-valerolactones
    Ryo 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...
  25. ncbi request reprint Preparation of arylzinc reagents and their use in the rhodium-catalyzed asymmetric 1,4-addition for the synthesis of 2-aryl-4-piperidones
    Ryo 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...
  26. doi request reprint Palladium-catalyzed decarboxylative [4 + 3] cyclization of gamma-methylidene-delta-valerolactones with 1,1-dicyanocyclopropanes
    Ryo 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...
  27. ncbi request reprint Rhodium-catalyzed asymmetric synthesis of 3,3-disubstituted 1-indanones
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    Angew Chem Int Ed Engl 46:3735-7. 2007
  28. doi request reprint Stereoselective synthesis of nipecotic acid derivatives via palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with imines
    Ryo 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...
  29. ncbi request reprint Chiral phosphine-olefin ligands in the rhodium-catalyzed asymmetric 1,4-addition reactions
    Wei 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...
  30. doi request reprint Rhodium-catalyzed asymmetric addition of arylboronic acids to beta-phthaliminoacrylate esters toward the synthesis of beta-amino acids
    Takahiro Nishimura
    Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606 8502, Japan
    J Am Chem Soc 132:464-5. 2010
    ....
  31. doi request reprint Enantioselective synthesis of α-tri- and α-tetrasubstituted allylsilanes by copper-catalyzed asymmetric allylic substitution of allyl phosphates with silylboronates
    Momotaro Takeda
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Org Chem 78:5007-17. 2013
    ..High regioselectivity has been achieved by employing NaOH as the base, and this catalyst system is effective for both γ-mono- and disubstituted allyl phosphates...
  32. ncbi request reprint A new entry of nucleophiles in rhodium-catalyzed asymmetric 1,4-addition reactions: addition of organozinc reagents for the synthesis of 2-aryl-4-piperidones
    Ryo 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...
  33. ncbi request reprint Organo[2-(hydroxymethyl)phenyl]dimethylsilanes as mild and reproducible agents for rhodium-catalyzed 1,4-addition reactions
    Yoshiaki Nakao
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    J Am Chem Soc 129:9137-43. 2007
    ....
  34. ncbi request reprint Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds
    Ryo 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...
  35. ncbi request reprint Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins
    Ryo Shintani
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    Angew Chem Int Ed Engl 45:3353-6. 2006
  36. doi request reprint Synthesis of quaternary carbon stereocenters by copper-catalyzed asymmetric allylic substitution of allyl phosphates with arylboronates
    Momotaro Takeda
    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
    J Org Chem 79:2354-67. 2014
    ....
  37. ncbi request reprint Catalytic enantioselective synthesis of beta-lactams: intramolecular Kinugasa reactions and interception of an intermediate in the reaction cascade
    Ryo Shintani
    Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
    Angew Chem Int Ed Engl 42:4082-5. 2003
  38. ncbi request reprint A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles
    Ryo 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...