Arai Laboratory, Department of Chemistry, Graduate School of Science, Chiba University

論文Original Articale


  1. Arai, T.; Tsuchida, T.; Miyazaki, T.; Awata, T. Catalytic Asymmetric Synthesis of Chiral 2-Vinylindole Scaffolds by FriedelCrafts Reaction. Org. Lett. 2017, 19, 758-761. [DOI: 10.1021/acs.orglett.6b03584]

  2. Kuwano, S.; Masuda, T.; Yamaguchi, K.; Arai, T. N-Heterocyclic Carbene-Promoted [3+2] Cycloaddition of Allenyl Sulfone and Arylidenemalononitriles. Heterocycles 2017, 95, 232-242. [DOI: 10.3987/COM-16-S(S)8]

  3. Arai, T.; Suzuki, T.; Inoue, T.; Kuwano, S. Chiral Bis(imidazolidine)iodobenzene (I-Bidine) Organocatalyst for Thiochromane Synthesis Using an Asymmetric Michael/Henry Reaction. Synlett 2017, 122-127. [DOI: 1055/s-0036-1588614].

  4. Arai, T.; Miyazaki, T.; Ogawa, H.; Masu, H. PyBidine-Ni(OAc)2-Catalyzed Michael/Aldol Reaction of Methyleneindolinones and Thiosalicylaldehydes for Stereochemically Divergent Thiochromanyl-spirooxindoles. Org. Lett. 2016, 18, 5824-5827 [DOI: 10.1021/acs.orglett.6b02783]- highlighted in SYNFACTS [jpg]

  5. Arai, T.; Kakino, J. Catalytic Asymmetric Synthesis of 3-Indolyl Methanamines Using Unprotected Indoles and N-Boc Imines under Basic Conditions. Angew. Chem. Int. Ed. 2016, 55, 1526315267 [DOI: 10.1002/anie.201607679]- highlighted in SYNFACTS [jpg]

  6. Touge, T.; Arai T. Asymmetric Hydrogenation of Unprotected Indoles Catalyzed by η6-Arene/N-Me-sulfonyldiamineRu(II) Complexes. J. Am. Chem. Soc. 2016, 138, 11299-11305 [DOI: 10.1021/jacs.6b06295] (Press Release) (News Paper) - highlighted in SYNFACTS [jpg]

  7. Arai, T.; Tokumitsu, C.; Miyazaki, T.; Kuwano, S.; Awata A. Catalytic Asymmetric [3+2]-Cycloaddition for Stereodivergent Synthesis of Chiral Indolyl-pyrrolidines. Org. Biomol. Chem. 2016, 14, 1831-1839 [DOI: 10.1039/ c5ob02278a].

  8. Sato, T.; Miyazaki, T.; Arai, T. Synthesis of Highly Functionalized Chiral Benzopyrano[3,4-c]pyrrolidines Bearing Five Contiguous Stereogenic Centers J. Org. Chem. 2015, 80, 10346-10352. [DOI: 10.1021/acs.joc.5b01445].

  9. Arai, T.; Watanabe, O.; Yabe, S.; Yamanaka, M. Catalytic Asymmetric Iodocyclization of N-Tosyl Alkenamides using Aminoiminophenoxy Copper Carboxylate: A Concise Synthesis of Chiral 8-Oxa-6-Azabicyclo[3.2.1]octanes. Angew. Chem. Int. Ed. 2015, 54, 12767-12771. [DOI: 10.1002/anie.201505748]. - highlighted in SYNFACTS [jpg]

  10. Arai, T.; Kojima, T.; Watanabe, O.; Itoh, T.; Kanoh, H. Recyclable poly-Zn3(OAc)4-3,3'-bis(aminoimino)binaphthoxide catalyst for asymmetric iodolactonization. ChemCatChem. 2015, 7, 3234-3238. [DOI: 10.1002/cctc.201500842]. - featured in "back cover picture" [link]

  11. Arai, T.; Moribatake T.; Masu H. Chiral Bis(imidazolidine)-derived NCN Pincer Rh Complex for Catalytic Asymmetric Mannich Reaction of Malononitrile with N-Boc Imines. Chem. Eur. J. 2015, 21, 10671-10675. [DOI: 10.1002/chem.201502097].

  12. Arai, T.; Tsuchiya, K.; Matsumura E. PyBidineNiCl2-Catalyzed Asymmetric Addition of Alcohols and Peroxides to Isatin-Derived Ketimines. Org. Lett. 2015, 17, 24162419. [DOI: 10.1021/acs.orglett.5b00928]

  13. Arai, T.; Ogawa, H.; Awata, A.; Sato, M.; Watabe, M.; Yamanaka, M. PyBidine-Cu(OTf)2-catalyzed asymmetric [3+2] cycloaddition using imino esters: Harmony of Cu-Lewis acid and imidazolidine-NH hydrogen-bonding in concerto catalysis. Angew. Chem. Int. Ed. 2015, 54,1595-1599. [DOI: 10.1002/anie.201410782]

  14. Arai, T.; Joko, A. Sato K. Design of a Chiral Secondary Amine Ligand for Cu-catalyzed anti-Selective Henry Reaction. Synlett, 2015, 26, 209-214. [DOI: 10.1055/s-0034-1379607]

  15. Awata, A.; Arai, T. PyBidine/Copper Catalyst: Asymmetric exo-Selective [3+2] Cycloaddition using Imino Ester and Electrophilic Indole. Angew. Chem. Int. Ed. 2014, 53, 10462-10465 [DOI: 10.1002/anie.201405223] - highlighted in SYNFACTS of the month [jpg]

  16. Arai, T.; Matsumura, E.; Masu, H. Bis(imidazolidine)pyridine-NiCl2 Catalyst for Nitro-Mannich Reaction of Isatin-Derived N-Boc Ketimines: Asymmetric Synthesis of Chiral 3-Substituted 3-Amino-2-oxindoles. Org. Lett. 2014, 16, 2768-8522. [DOI: 10.1021/ol501085y] - highlighted in SYNFACTS [jpg]

  17. Arai, T.; Sugiyama, N.; Masu, H.; Kado, S.; Yabe, S.; Yamanaka, M. Trinuclear Zn3(OAc)4-3,3-bis(aminoimino)binaphthoxide Complex for Highly Efficient Catalytic Asymmetric Iodolactonization. Chem. Comm. 2014, 42, 8287-8290. [DOI: 10.1039/C4CC02415J] - featured in "cover picture" [link]

  18. Arai, T.; Matsumura, E. Switching Enantioface Selection in the Asymmetric Nitro-Mannich Reaction Using Single Chiral Bis(imidazolidine)pyridine-metal Catalysts. Synlett 2014, 25, 1776-1780. [DOI: 10.1055/s-0034-1378204]

  19. Arai, T.; Yamamoto, Y. Diversity-Oriented Asymmetric Catalysis (DOAC): Stereochemically Divergent Synthesis of Thiochromanes Using an Imidazoline-Aminophenol-Nickel Catalyzed Michael/Henry Reaction. Org. Lett. 2014, 16, 1700-1703. [DOI: 10.1021/ol500361w] - highlighted in SYNFACTS [jpg]

  20. Awata, A.; Wasai, M.; Masu, H.; Kado, S.; Arai, T. Imidazoline-aminophenol (IAP)-nickel complex: Structure and catalytic activity in enantioselective 1,4-addition of 3'-indolyl-3-oxindoles to nitroethylene. Chem. Eur. J. 2014, 20, 2470-2477. [DOI: 10.1002/chem.201304456]

  21. Sato, T.; Arai, T. Chiral Bis(oxazolidine)pyridine-Cu-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indole with Nitroalkenes. Synlett, 2014, 25, 349-354. [DOI: 10.1055/s-0033-1340311] - highlighted in SYNFACTS [jpg]

  22. Oyama, S.; Fujino, H.; Yamazaki, R.; Okura, I.; Regan, J. W.; Awata, A.; Arai, T.; Murayama, T. Novel indole compound, AWT-489, inhibits prostaglandin D2-induced CD55 expression by acting on DP prostanoid receptors as an antagonist in LS174T human colon cancer cells, Archives of Biochemistry and Biophysics. 2014, 541, 21-29. [link]

  23. Arai, T.; Kajikawa, S.; Matsumura, E. The Role of Ni-carboxylate During Catalytic Asymmetric Iodolactonization Using PyBidine-Ni(OAc)2. Synlett, 2013, 24, 2045-2048.[DOI: 10.1055/s-0033-1339676]

  24. Arai, T. Catalytic Asymmetric [3+2]-Cycloaddition Reaction for Controlling Multiple Stereogenic Centers on Pyrrolidines. J. Synth. Org. Chem, Japan. 2013, 71, 672-682.

  25. Arai, T.; Ogino, Y.; Sato, T. Developmet of a Tailor-made Bis(oxazolidine)pyridine-metal Catalyst for the [3+2] Cycloaddition of Azomethine Imines with Propiolates. Chem. Commun. 2013, 49, 7776-7778.[DOI: 10.1039/C3CC44354J] - featured in "inside back cover" [link], highlighted in SYNFACTS [jpg]

  26. Arai, T.; Y. Yamamoto; Awata, A.; Kamiya, K.; Ishibashi, M.; Arai, M. A. Catalytic Asymmetric Synthesis of Mixed 3,3'-Bisindoles and Their Evaluation as Wnt Signaling Inhibitors. Angew. Chem. Int. Ed. 2013, 52, 2486-2490.[DOI: 10.1002/anie201208918] - selected as Hot Paper [Link] and highlighted in SYNFACTS [jpg]

  27. Arai, T.; Oka, I.; Morihata, T.; Awata, A.; H. Masu. A Neutral, Chiral, Bis(imidazolidine)-derived NCN-type Palladium Pincer Complex Demonstrating Catalyst Activity.Chem. Eur. J. 2013, 19, 1554-1557.[DOI: 10.1002/chem.201204017] - Most Accessed Articles: January 2013[link]

  28. Awata, A.; Arai, T. Catalytic Asymmetric Cyclopropanation with Diazooxindole. Synlett, 2013, 24, 29-32.[DOI: 10.1055/s-0032-1317746]-highlighted in SYNFACTS [jpg]

  29. Arai, T.; Mishiro, A.; Matsumura, E.; Awata, A.; Shirasugi, M. syn-Selective Asymmetric Mannich Reaction of Sulfonyl Imines with Iminoesters Catalyzed by the N,N,N-Tridentate PyBidine-Cu(OTf)2 Complex. Chem. Eur. J. 2012, 18, 11219-11222.[DOI: 10.1002/chem.201201537]

  30. Awata, A.; Arai, T. Catalytic Asymmetric Exo'-selective [3+2] Cycloaddition for Constructing Stereochemically Diversified Spiro[pyrrolidin-3,3'-oxindoles. Chem. Eur. J.2012, 18, 8278-8282.[DOI: 10.1002/chem.201201249]

  31. Arai, T.; Ogino, Y. Chiral Bis(Imidazolidine)Pyridine-Cu Complex-Catalyzed Enantioselective [3+2]-Cycloaddition of Azomethine Imines with Propiolates. Molecules, 2012, 17, 6170-6178.[DOI: 10.3390/molecules17056170]

  32. Arai, T.; Kawasaki, N.; Kanoh, H. Magnetically Separable Cu-carboxylate MOF Catalyst for Henry Reaction. Synlett. 2012, 1549-1553.[DOI: 10.1055/s-0031-1290935]

  33. Arai, T.; Sakagami, K. Asymmetric Banzoylation of meso-Hydrobenzoin Using a Reusable Tripodal Imidazoline-Pyridine-Cu Catalyst. Eur. J. Org. Chem. 2012, 1097-1100.[DOI: 10.1002/ejoc.201101722]

  34. Arai, T.; Awata, A.; Wasai, M.; Yokoyama, N.; Masu, H. Catalytic Asymmetric Friedel-Crafts/Protonation of Nitroalkenes and N-Heteroaromatics. J. Org. Chem. 2011, 76, 5450-5456. [DOI: 10.1021/jo200546a]-highlighted in SYNFACTS [pdf]

  35. Arai, T.; Wasai, M.; Yokoyama, N. Easy Access to Fully Functionalized Chiral Tetrahydro-β-Carboline Alkaloids. J. Org. Chem. 2011, 76, 2909-2912. [DOI: 10.1021/jo1025833]

  36. Arai, T.; Yokoyama, N.; Mishiro, A.; Sato, H. Catalytic Asymmetric Exo'-Selective [3+2] Cycloaddition of Iminoesters with Nitroalkenes. Angew. Chem. Int. Ed. 2010, 49, 7895-7898. [DOI: 10.1002/anie.201004098]- highlighted as SYNFACTS of the Months [pdf]

  37. Arai, T.; Taneda, Y.; Endo,Y. Formation of Multi-stereogenic Centers Using a Catalytic Aymmetric Henry Reaction. Chem. Commun. 2010, 46, 7936-7938. [DOI: 10.1039/C0CC03022H]

  38. Arai, T.; Ikematsu, Y.; Suemitsu, Y. Nickel-catalyzed multicomponent coupling reaction using ynones. Pure Appl. Chem. 2010, 82, 1485-1490. [DOI: 10.1351/PAC-CON-09-09-08]

  39. Arai, T.; Mishiro, A.; Yokoyama, N.; Suzuki, K.; Sato, H. Chiral Bis(imidazolidine)pyridine-Cu(OTf)2: Catalytic Asymmetric Endo-Selective [3+2] Cycloaddition of Imino Esters with Nitroalkenes. J. Am. Chem. Soc. 2010, 132, 5338-5339. [DOI: 10.1021/ja100265j]

  40. Arai, T. Solid-phase Catalysis/CD-HTS: A Powerful Technology Platform for Exploring Novel Asymmetric Catalysts. J. Synth. Org. Chem., Jpn, 2010, 68, 19-32.

  41. Arai, T.; Suzuki, K. Design and Synthesis of Chiral Imidazolidine-Pyridine Ligands. Synlett 2009, 3167-3170.[DOI: 10.1055/s-0029-1218311]

  42. Yanagisawa, A.; Satou, T.; Izumiseki, A.; Tanaka, Y.; Miyagi, M.; Arai, T.; Yoshida, K. Methanol-Assisted Catalysis by Chiral Tin Methoxides: An Alternative Asymmetric Aldol Process. Chem. Eur. J. 2009, 15, 11450-11453.[DOI: 10.1002/chem.200901822]

  43. Yokoyama, N.; Arai, T. Asymmetric Friedel-Crafts reaction of N-heteocycles and nitroalkenes catalyzed by imidazoline-aminophenol-Cu complex. Chem. Commun. 2009, 3285-3287.[DOI: 10.1039/b904275j]-highlighted in SYNFACTS [pdf]

  44. Yanqagisawa, A.; Matsumoto, T.; Arai, T.; Yoshida, K. Dibutyltin Dibromide-catalyzed Trimethylsilylcayanation of Aldehydes and Imines. Chem. Lett. 2009, 38, 336-337.[DOI: 10.1246/cl.2009.336]

  45. Takizawa, S.; Arai, T.; Sasai, H. Development of Novel Immobilization Methods for Multicomponent Asymmetric Catalyst (MAC). J. Synth. Org. Chem., Jpn, 2009, 67, 194-207.

  46. Arai, T.; Suemitsu, Y.; Ikematsu, Y. Ni(0)-Catalyzed Conjugate Addition of Me3SiCN to Ynones: α-Bromo-β-cyano Tetrasubstituted Enones. Org. Lett. 2009, 11, 333-335.[DOI: 10.1021/ol802508q]

  47. Arai, T.; Mizukami, T.; Mishiro, A.; Yanagisawa, A. Kinetic Resolution of 1,2-Diols Using Nitrogen-Tethered Bisimidazoline-Copper(I) Catalyzed Benzoylation. Heterocycles, 2008, 76, 995-1000.[abstract]

  48. Yanagisawa, A.; Izumi, Y.; Arai, T. Michael Addition Reaction of Alkenyl Trichloroacetates Catalyzed by Dibutyltin Dimethoxide. Chem. Lett. 2008, 37, 1092-1093. [DOI: 10.1246/cl.2008.1092]

  49. Yanagisawa, A.; Suzuki, T.; Koide, T.; Okitsu, S.; Arai, T. Selective Propargylation of Carbonyl Compounds and Imines with Barium Reagents. Chem. Asian J. 2008, 3, 1793-1800. [DOI:10.1002/asia.200800264]

  50. Arai, T.; Yokoyama, N. Tandem Catalytic Asymmetric Friedel-Crafts/Henry Reaction: Acyclic Three Contiguous Stereocenters. Angew. Chem. Int. Ed. 2008, 47, 4989-4992.[DOI: 10.1002/anie.200801373]-selected as Hot Paper & highlighted in SYNFACTS[pdf]

  51. Arai, T.; Takashita, R.; Endo, Y.; Watanabe, M. Yanagisawa, A. Aymmetric syn-Selective Henry Reaction Catalyzed by Sulfonyldiamine-CuCl-Pyridine System. J. Org. Chem.2008, 73, 4903-4906. [DOI: 10.1021/jo800412x]-highlighted in SYNFACTS [pdf]

  52. Arai, T.; Yokoyama, N.; Yanagisawa, A. A Library of Chiral Imidazoline-Aminophenols: Discovering an Efficient Reaction Sphere. Chem. Eur. J. 2008, 14, 2052-2059.[DOI: 10.1002/chem.200701439]

  53. Yanagisawa, A.; Arai, T. Recent advances in chiral phosphine-silver(I) complex-catalyzed asymmetric reactions. Chem. Commun. 2008, 1165-1172. [DOI: 10.1039/b717104h]

  54. Arai, T.; Sato, T.; Kanoh, H.; Kaneko, K.; Oguma, K.; Yanagisawa, A. Organic-Inorganic Hybrid Polymer-Encapsulated Magnetic Nanobeads Catalysts. Chem. Eur. J. 2008, 14, 882-885.[DOI:10.1002/chem.200701371]-highlighted in SYNFACTS[pdf]

  55. Arai, T.; Watanabe, M.; Yanagisawa, A. Practical Asymmetric Henry Reaction Catalyzed by a Chiral Diamine-Cu(OAc)2 Complex. Org. Lett. 2007, 9, 3595-3597. [DOI: 10.1021/ol7014362]

  56. Miura, T.; Natsume, S.; Kanemoto, K.; Atsumi, K.; Fushimi, H.; Sasai, H.; Arai, T.; Yoshida, T.; Ajito, K. Novel Azalides Derived from Sixteen-Membered Macrolides. J. Antibiot. 2007, 60, 407-435.

  57. Yanagisawa A.; Takahashi, H.; Arai, T. One-pot synthesis of 1,5-diketones by barium isopropoxide. Tetrahedron, 2007, 63, 8581-8585.

  58.  Arai, T.; Mizukami, T.; Yanagisawa, A. Reaction Optimization Using Solid Catalysis-CD HTS: Nb-Imidazoline-Cu(I) Catalyzed Asymmetric Benzoylation of meso-1,2-Diols. Org. Lett. 2007, 9, 1145-1147. [DOI: 10.1021/ol0702122]

  59. Arai, T.; Endo, Y.; Yanagisawa, A. Salicylhydrazone ligands for enantioselective addition of diethylzinc to aldehydes Tetrahedron: Asymmetry 2007, 18, 165-169.[DOI:10.1016/j.tetasy.2007.01.022]

  60. Yanagisawa, A.; Shinohara, A.; Takahashi, H.; Arai, T. Barium Hydride Promoted Homocoupling and Cross-Coupling Reactions of Enones: An Alternative Entry to Diels-Alder Adducts. Synlett, 2007, 141-145.

  61. Yanagisawa, A.; Ichikawa, T.; Arai, T. Dibutyltin Dimethoxide and BINAPSilver(I) Complex-catalyzed Asymmetric Aldol Reaction of Alkenyl Trichloroacetates with Aldehydes. J. Orgnomet. Chem. 2007, 550-553.

  62. Takahashi, H.; Arai, T.; Yanagiswa, A. 1,5-Diketone Synthesis Promoted by Barium Hydride or Barium Alkoxides. Synlett, 2006, 2833-2835.

  63. Arai, T.; Sato, T.; Kanoh, H.; Kaneko, K.; Yanagisawa A. Direct α-Hydroxylation of Ketones Catalyzed by Organic-Inorganic Hybrid Polymer. Chem. Lett. 2006, 35, 1094-1095.

  64. Yanagisawa, A.; Aoki, T.; Arai, T. Dibutyltin Oxide-Catalyzed Allyl Transfer Reaction to Aldehydes. Synlett, 2006, 2071-2074.

  65. Arai, T.; Watanabe, M.; Fujiwara, A.; Yokoyama, N.; Yanagisawa, A. Direct Monitoring of Asymmetric Induction of Solid Phase Catalysis Using Circular Dichroism: Diamine-Cu(I) Catalyzed Asymmetric Henry Reaction. Angew. Chem. Int. Ed. 2006, 45, 5978-5981.-highlighted in SYNFACTS[pdf]

  66. Jayaprakash, D.; Takizawa, S.; Arai, T.; Sasai, H. Development of efficient methods for the immobilization of multicomponent asymmetric catalysts. Journal of Experimental Nanoscience, 2006, 1, 477-510.

  67. Yanagisawa, A.; Touge, T.; Arai, T.  Asymmetric protonation of silyl enolates catalyzed by chiral phosphine-silver(I) complexes. Pure and Applied Chemistry, 2006, 78, 519-523.

  68. Mitsuhashi, K.; Ito, R.; Arai, T.; Yanagisawa, A. Catalytic Asymmetric Protonation of Lithium Enolates Using Amino Acid Derivatives as Chiral Proton Sources. Org. Lett. 2006, 8, 1721-1724.

  69. Arai, T.; Fujiwara, A.; Watanabe, M.; Yokoyama, N.; Fujito, T.; Deguchi, K.; Yanagisawa A. Quality Control of Solid-Phase Synthesis: 13C PST/MAS NMR Analysis on Non-destructed SynPhase Lantern. Tetrahedron Lett. 2006, 47, 1673-1677.

  70. Arai, T.; Takasugi, H.; Sato, T.; Noguchi, H.; Kanoh, H.; Kaneko, K.; Yanagisawa A. Catalytic Synthesis of α-Hydroxy Ketones Using Organic-Inorganic Hybrid Polymer. Chem. Lett. 2005, 34, 1590-1591.

  71. Yanagisawa, A.; Saito, H.; Harada, M.; Arai, T. Mannich-Type Reaction Using Alkenyl Trichloroacetates Catalyzed by Dibutyltin Dimethoxide. Adv. Synth. Catal., 2005, 347, 1517-1522.

  72. Arai, T.; Mizukami, T.; Yokoyama, N.; Nakazato, D.; Yanagisawa, A. Design and Synthesis of a Chiral N-tethered Bis(imidazoline) Ligand. Synlett, 2005, 2670-2672.

  73. Yanagisawa, A.; Okitsu, S.; Arai, T. Regioselective Propargylation of Carbonyl Compounds with (3-Bromo-prop-1-ynyl)trimethylsilane Promoted by Reactive Barium. Synlett, 2005, 1679-1682.

  74. Yanagisawa, A.; Touge, T.; Arai, T. Enantioselective Protonation of Silyl Enolates Catalyzed by BINAP-AgF Complex. Angew. Chem. Int. Ed. 2005, 44, 1546-1548.

  75. Kim, Y-K.; Arai, M. A.; Arai, T.; Lamenzo, J. O.; Dean III, E. F.; Patterson, P. A.; Clemons, P. A.; Schreiber, S. L. Relationship of Stereochemical and Skeletal Diversity to Cellular Measurement Space. J. Am. Chem. Soc. 2004, 126, 14740-14745.

  76. Yanagisawa, A.; Goudu, R.; Arai, T. Selective Synthesis of α,β-Unsaturated Ketones by Dibutyltin Dimethoxide-catalyzed Condensation of Aldehydes with Alkenyl Trichloroacetates. Org. Lett., 2004, 6, 4281-4283.

  77. Yanagisawa, A.; Nakamura, Y.; Arai, T. α-Amino Acid-promoted Asymmetric Allylation of Aldehydes with Allylstannanes. Tetrahedron: Asymmetry, 2004,15, 1909-1913.

  78. Yanagisawa, A.; Takahashi, H.; Arai, T. Reactive Barium-promoted Reformatsky-type Reaction of α-Chloroketones with Aldehydes. Chem. Commun. 2004, 580-581.

  79. Arai, M.; Shinohara, T.; Arai, T.; Sasai, H. Development of the First Spiro Bis(isoxazoline) Ligands (SPRIXs) and Their Applications to Catalytic Enantioselective Reactions. J. Synth. Org. Chem, Japan. 2004, 62, 61-69.