Novel Chiral Bifunctional Heterogeneous Catalysts for Asymmetric Tandem Reactions

• Project Area: Advanced Molecular Transformations by Organocatalysts
• Project/Area Number: 26105711
• Research Category: Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
• Allocation Type: Single-year Grants
• Review Section: Science and Engineering
• Research Institution: The University of Tokyo
• Principal Investigator: ユー ウージン 東京大学, 理学(系)研究科(研究院), 助教 (70626077)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥6,760,000 (Direct Cost: ¥5,200,000、Indirect Cost: ¥1,560,000); Fiscal Year 2015: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000); Fiscal Year 2014: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
• Keywords: heterogeneous catalysis / organocatalysis / asymmetric catalysis / aerobic oxidation / metal nanoparticles / aerobic oxidaiton

Outline of Annual Research Achievements

Over the fiscal year, we have been investigating the fabrication of a chiral heterogeneous bifunctional catalyst that is capable of performing an asymmetric tandem oxidation process (TOP). We were able to combine gold/palladium nanoparticles (NPs) with a polymer-supported chiral phosphoric acid (CPA) catalyst, and this composite material possessed the capacity to catalyze the sequential aerobic oxidation-asymmetric aza-Friedel Crafts reaction. We were able to perform this asymmetric TOP to obtain various chiral piperazines in high yields and enantioselectivites. In addition, we were able to recover and reuse the heterogeneous several times without significant loss in yields and enantioselectivites.

Research Progress Status

27年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

27年度が最終年度であるため、記入しない。

Research Products

• [Presentation] Combined Heterogeneous Catalysts (Au/Pd NP-chiral Bronsted Acid-polymer) for a Tandem Asymmetric Aerobic Oxidation-Aza-Friedel-Crafts Process (2016)
  • Author(s): Javier Miguelez, Honggang Cheng, Woo-Jin Yoo, Hiroyuki Miyamura, Shu Kobayashi
  • Organizer: 96th Annual Meeting of the Chemical Society of Japan
  • Place of Presentation: 同志社大学京田辺キャンパス（京都府京田辺市）
  • Year and Date: 2016-03-24
• [Presentation] Novel Chiral Bifunctional Heterogeneous Catalysts for Asymmetric Tandem Reactions (2016)
  • Author(s): Woo-Jin Yoo
  • Organizer: 6th Symposium on Advanced Molecular Transformations by Organocatalysis
  • Place of Presentation: 大阪科学技術センター中ホール（大阪府大阪市）
  • Year and Date: 2016-01-22
  • Invited
• [Presentation] Sequential Aerobic Oxidation/Intramolecular Asymmetric Aza-Friedel Crafts Reaction Enabled by a Chiral Bifunctional Heterogeneous Catalyst (2015)
  • Author(s): Woo-Jin Yoo, Honggang Cheng, Hiroyuki Miyamura, Shu Kobayashi
  • Organizer: 第8回有機触媒シンポジウム兼「有機分子触媒による未来型分子変換」第5回公開シンポジウム
  • Place of Presentation: Naha, Japan
  • Year and Date: 2015-05-10 – 2015-05-11
• [Presentation] Preparation and Evaluation of Polymer-Immobilized Chiral Phosphoric Acids for Catalytic Asymmetric Intramolecular Aza-Friedel-Crafts Reaction (2015)
  • Author(s): Woo-Jin Yoo, Honggang Cheng, Hiroyuki Miyamura, Shu Kobayashi
  • Organizer: 95th Annual Meeting of the Chemical Society of Japan (CSJ)
  • Place of Presentation: Tokyo, Japan
  • Year and Date: 2015-03-26 – 2015-03-29