Development of Chiral Tetraaminophosphonium Peroxyacids for Asymmetric Catalyses

• Project/Area Number: 23655080
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Nagoya University
• Principal Investigator: URAGUCHI Daisuke 名古屋大学, 工学研究科, 准教授 (70426328)
• Project Period (FY): 2011 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000); Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2011: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 有機分子触媒 / 酸化反応 / 不斉合成 / 過オキソ酸イオン / ホスホニウムイオン / 過酸化水素 / イオン対 / 酸化 / オキソ酸

Research Abstract

Novel chiral salts which are constructed from P-spiro chiral aminophosphonium ion and peroxoacid ions were achieved. It was revealed that the salts can be used for oxidation reactions. In addition, we found the ability of chiral iminophosphorane for activating hydrogen peroxide and applied this fact to develop asymmetric oxidation of N-sulfonyl imines.

Research Products

• [Journal Article] Catalytic Asymmetric Oxidation of N-Sulfonyl Imines with Hydrogen Peroxide-Trichloroacetonitrile System (2013)
  • Author(s): Daisuke Uraguchi, Ryosuke Tsutsumi, Takashi Ooi
  • Journal Title: Journal of the American Chemical Society Volume: 135 Issue: 22 Pages: 8161-8164
  • DOI: 10.1021/ja403491j
  • Peer Reviewed
• [Journal Article]
  • Author(s): 堤 亮祐, 浦口 大輔, 大井 貴史
  • Journal Title: 月刊化学 Volume: (印刷中)
• [Presentation] 過酸化水素を用いた N-スルホニルイミンの触媒的不斉酸化反応 (2013)
  • Author(s): 堤 亮祐, 浦口 大輔, 大井 貴史
  • Organizer: 日本化学会第93 春季年会
  • Place of Presentation: 滋賀
  • Year and Date: 2013-03-22
• [Presentation] 過酸化水素を用いたN-スルホニルイミンの触媒的不斉酸化反応 (2013)
  • Author(s): 堤 亮祐・浦口 大輔・大井 貴史
  • Organizer: 日本化学会春季年会９２
  • Place of Presentation: 立命館大学 びわこ・草津キャンパス
• [Presentation] Late-Stage Activation Strategy for Asymmetric Oxidation with Hydrogen Peroxide: Application to the Synthesis of Chiral Oxaziridines (2012)
  • Author(s): 堤 亮祐, 浦口 大輔, 大井 貴史
  • Organizer: 1stJapan-USA Organocatalytic Symposium in Hawaii (2012)
  • Place of Presentation: ハワイ, 米国
  • Year and Date: 2012-12-17
• [Presentation] Catalytic Enantioselective Oxidation of N-Sulfonyl Imines Using Hydrogen Peroxide (2012)
  • Author(s): 堤 亮祐, 浦口 大輔, 大井 貴史
  • Organizer: IKCOC-12
  • Place of Presentation: 京都
  • Year and Date: 2012-11-16
• [Presentation] Late-Stage Activation Strategy for Asymmetric Oxidation with Hydrogen Peroxide: Application to the Synthesis of Chiral Oxaziridines (2012)
  • Author(s): Ryosuke Tsutsumi, Daisuke Uraguchi, Takashi Ooi
  • Organizer: 1st Japan-USA Organocatalytic Symposium in Hawaii (2012)
  • Place of Presentation: Hawaii
• [Presentation] Catalytic Enantioselective Oxidation of N-Sulfonyl Imines Using Hydrogen Peroxide (2012)
  • Author(s): Ryosuke Tsutsumi, Daisuke Uraguchi, Takashi Ooi
  • Organizer: IKCOC-12
  • Place of Presentation: Kyoto