Development of the oxidative asymmetric catalysis by using transition metal complexes

• Project/Area Number: 24550128
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: The Institute of Physical and Chemical Research
• Principal Investigator: SOHTOME Yoshihiro 独立行政法人理化学研究所, 袖岡有機合成化学研究室, 研究員 (50431888)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Project Status: Completed (Fiscal Year 2014)
• Budget Amount: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000); Fiscal Year 2014: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000); Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000); Fiscal Year 2012: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
• Keywords: 遷移金属錯体 / 酸化 / 酸素 / 有機合成化学 / 不斉触媒 / 遷移金属 / 不斉合成

Outline of Final Research Achievements

In order to develop catalytic systems that can be applied to various asymmetric reactions, the development of catalytic reactions based on new concepts is significant. Here, we have successfully developed two distinct aerobic oxidative functionalizations of N-Boc oxindoles including α-hydroxylation and oxidative hetero carbon-carbon bond-forming reactions by exploiting use of our original Pd complex.

Research Products

• [Journal Article] Sequential stereodivergent organocatalysis and programmed organocascade (2014)
  • Author(s): Yoshihiro Sohtome and Kazuo Nagasawa
  • Journal Title: Org. Biomol. Chem. Volume: 12 Issue: 11 Pages: 1681-1685
  • DOI: 10.1039/c3ob42310g
  • Peer Reviewed
• [Journal Article] Asymmetric Michael Reaction of Nitroolefins with b-Dicarbonyl Compounds Catalysed by 1,3-Diamine-Tethered Guanidine-Thiourea Bifunctional Organocatalysts (2014)
  • Author(s): Natsuko Horitsugi, Kohei Kojima, Koji Yasui, Yoshihiro Sohtome, Kazuo Nagasawa
  • Journal Title: Asian. J. Org. Chem. Volume: 3 Issue: 4 Pages: 445-448
  • DOI: 10.1002/ajoc.201402002
  • Peer Reviewed
• [Journal Article] Selenium-Based S-Adenosylmethionine Analog Reveals the Mammalian Seven-Beta-Strand Methyltransferase METTL10 to Be an EF1A1 Lysine Methyltransferase (2014)
  • Author(s): Tadahiro Shimazu, Joaquin Barjau, Yoshihiro Sohtome, Mikiko Sodeoka, Yoichi Shinkai
  • Journal Title: PLOSONE Volume: 9 Issue: 8 Pages: e105394-e105394
  • DOI: 10.1371/journal.pone.0105394
  • Peer Reviewed / Open Access
• [Journal Article] Sequential Enantiodivergent Organocatalysis: Reversibility in Enantioswitching Controlled by a Conformationally Flexible Guanidine/Bisthiourea Organocatalyst (2013)
  • Author(s): Yoshihiro Sohtome, Takahisa Yamaguchi, Shinji Tanaka and Kazuo Nagasawa
  • Journal Title: Organic & Biomol. Chem. Volume: 11 Issue: 17 Pages: 2780-2786
  • DOI: 10.1039/c3ob27479a
  • Peer Reviewed
• [Journal Article] Epidithiodiketopiperazine as a pharmacophore for protein lysine methyltransferase G9a inhibitors: Reducing cytotoxicity by structural simplification (2013)
  • Author(s): Shinya Fujishiro
  • Journal Title: Bioorg. Med. Chem. Lett. Volume: 23 Issue: 3 Pages: 733-736
  • DOI: 10.1016/j.bmcl.2012.11.087
  • Peer Reviewed
• [Presentation] パラジウム触媒を用いるオキシインドール類の酸化的ヘテロカップリング反応 (2015)
  • Author(s): 澤村美紀、北條大樹、Akindele Tito、五月女宜裕、袖岡幹子
  • Organizer: 日本化学会 第95春季年会
  • Place of Presentation: 日本大学理工学部 船橋キャンパス／薬学部
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] Exploring chemical strategies to control chiral environments constructed by molecular catalysts and enzymes (2015)
  • Author(s): Yoshihiro SOHTOME
  • Organizer: Workshop on Chirality in Chiba University 3rd Symposium
  • Place of Presentation: Chiba University
  • Year and Date: 2015-03-10
  • Invited
• [Presentation] α-ケトエステルと(E)-ニトロンを用いる触媒的不斉[3+2]環化付加型反応の開発: 歪みを内包するキラルニッケル-ジアミン錯体触媒の創製 (2014)
  • Author(s): 五月女宜裕、中村元太、 LECTARD Sylvain、土本晃久、村中厚哉、内山真伸、橋爪大輔、 袖岡幹子
  • Organizer: 第40回反応と合成の進歩シンポジウム
  • Place of Presentation: 東北大学川内萩ホール
  • Year and Date: 2014-11-10 – 2014-11-11
• [Presentation] オキシインドールを基質とする酸化的エノラートカップリング反応の開発 (2014)
  • Author(s): 澤村美紀、北條大樹、Akindele Tito、五月女宜裕、袖岡幹子
  • Organizer: 第4回CSJ化学フェスタ2014
  • Place of Presentation: タワーホール船堀
  • Year and Date: 2014-10-14 – 2014-10-16
• [Presentation] 有機触媒・金属触媒・酵素を用いる分子空間制御 (2014)
  • Author(s): 五月女宜裕
  • Organizer: 「精密物質変換のための分子空間化学」キックオフシンポジウム
  • Place of Presentation: 東京理科大学神楽坂キャンパス
  • Year and Date: 2014-08-30
  • Invited
• [Presentation] ニッケル-ジアミン触媒を活用した (E)-ニトロンとα－ケトエステルの不斉[3+2]環化付加型反応: アキラル塩基の効果と反応機構の検討 (2014)
  • Author(s): 中村元太、五月女宜裕、Lectard Sylvain、土本晃久、袖岡幹子
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋
• [Presentation] パラジウム触媒を活用した酸素を用いるオキシインドールの触媒的不斉ヒドロキシル化反応 (2014)
  • Author(s): 北條大樹、Akindele Tito、五月女宜裕、袖岡幹子
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋
• [Presentation] Solvent-Dependent Enantioswitching in Mannich-Type reactions Using Conformationally Flexible Guanidine/Bisthiourea Organocatalyst (2013)
  • Author(s): Sohtome, Y.; Nagasawa, K.
  • Organizer: 15th Asian Chemical Congress
  • Place of Presentation: Kuala Lumpur, Singapore
  • Invited
• [Presentation] ニッケル-ジアミン触媒を活用したα－ケトエステルを用いるイソオキサゾリジンの触媒的不斉合成 (優秀ポスター発表賞)
  • Author(s): 中村元太、五月女宜裕、Lectard Sylvain、土本晃久、袖岡幹子
  • Organizer: 第3回CSJ化学フェスタ2013
  • Place of Presentation: 船堀
• [Remarks] 袖岡有機合成化学研究室
  • URL: http://soc.riken.jp/