Transfer from plnar chirality to axial chirality

• Project/Area Number: 19550053
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kyoto Pharmaceutical University
• Principal Investigator: UEMURA Motokazu Kyoto Pharmaceutical University, 薬学部, 客員教授 (90047241)
• Project Period (FY): 2007 – 2008
• Project Status: Completed (Fiscal Year 2008)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2008: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2007: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
• Keywords: 有機合成 / 面不斉 / 軸不斉 / 触媒反応 / 金触媒 / アレーンクロム錯体 / 環化異性化反応 / エンイン化合物 / 不斉転写反応 / アレークロム錯体 / 金(I)触媒 / 環化反応 / オルトリチオ化

Research Abstract

エンイン結合を有する面不斉アレーンクロム錯体を金(I)触媒を用いてcycloisomerizationを行い、軸不斉ビアリール化合物を合成した。基質としてアルキン部に二つの芳香環が結合したアレーンクロム錯体、及びアルケン部に二つの芳香環が結合した2種のクロム錯体を用いた。いずれの基質も立体選択的にcycloisomerization反応が進行し、anti-ビアリールクロム錯体が高収率で得られ、軸不斉ビアリール化合物を光学活性体として合成することができた。

Research Products

• [Journal Article] Regiochemical Observations Depending on Electrophiles in Directed Lithiation of 1,3-Diheteroatom Substituted Arene Tricarbonylchromium Complex (2009)
  • Author(s): C. Michon, M. Murai, M. Nakatsu, J. Uenishi
  • Journal Title: Tetrahedron 65 Pages: 752-756
  • Peer Reviewed
• [Journal Article] Regiochemical Observations Depending on Electrophiles in Directed Lithiation of 1, 3-Diheteroatom Substituted Arene Tricar bonylchromium Complexes (2009)
  • Author(s): C. Michon, M. Murai, M. Nakatsu, J. Uenishi, M. Uemura
  • Journal Title: Tetrahedron 65 Pages: 752-756
  • Peer Reviewed
• [Journal Article] Cycloisomerization of (Arene)chromium Complexes with Enyne by Gold(I) Catalyst for Axially Chiral Biaryl (2008)
  • Author(s): C. Michon, S. Liu, S. Hiragushi, J. Uenishi, M. Uemura
  • Journal Title: Tetrahedron 64 Pages: 11756-11762
  • Peer Reviewed
• [Journal Article] Gold(I)-Catalyzed Cycloisomerization of Arene Chromium Complexes with Enyne Bonds Directed Towards Axially Chiral Biaryls (2008)
  • Author(s): C. Michon, S. Liu, S. Hiragushi, J. Uenishi, M. Uemura
  • Journal Title: Synlett Pages: 1321-1324
  • Peer Reviewed
• [Journal Article] Gold(I)-Catalyzed Cycloisomerization of Arene Chromium Complexes with Enyne Bonds Directed Towards Axially Chiral Biaryls (2008)
  • Author(s): C. Michon, S. Liu, S. Higushi, J. Uenishi, M. Uemura
  • Journal Title: Synlett Pages: 1321-1324
  • Peer Reviewed
• [Journal Article] Isomerization of (Arene) chromium Complexes with Enyne by Gold(I) Catalyst for Axially Chiral Biaryl (2008)
  • Author(s): C. Michon, S. Liu, S. Higushi, J. Uenishi, M. Uemura
  • Journal Title: Tetrahedron 64 Pages: 11756-11762
  • Peer Reviewed
• [Journal Article] Cycloisomerization of(Arene)chromium Complexes with Enyneby Gold(I)catalyst for Axially Chiral Biaryl (2008)
  • Author(s): C.Michon, S.Liu, S.Hiragushi, J.Uenishi, M.Uemura
  • Journal Title: Synlett
  • Peer Reviewed
• [Journal Article] Stereoselective Synthesis of Both Enantiomers of N-Aryl Indoles with Axially Chiral N-C Bonds (2007)
  • Author(s): K. Kamikawa, S. Kinoshita, M. Furusyo, S. Takemoto, H. Matsuzaka, M. Uemura, J. Org
  • Journal Title: J. Org.Chem. 72 Pages: 3394-3402
  • Peer Reviewed
• [Journal Article] Stereoselective tricarbonylchromium Migration Reactions in Axially Chiral Biaryl Chromium Complexes (2007)
  • Author(s): K. Kamikawa, K. Nishino, T. Sakamoto, S. Kinoshita, H. Matsuzaka, M. Uemura, J. Organomet
  • Journal Title: J.Organomet. Chem. 692 Pages: 678-684
  • Peer Reviewed
• [Journal Article] Stereoselective tricarbonylckromium Migration Reacdons in Axially Chlral Biaryl Chromium Complexes (2007)
  • Author(s): K.Kamikawa, K.Nishino, T.Sakamoto, S.Kinoshita, H.Matsuzaka, M.Uemura
  • Journal Title: J, Organomet.Chem 692 Pages: 678-684
  • Peer Reviewed
• [Journal Article] Stereoselective Synthesis of Both Enantiomers of N-Ary Indoles with Axially Chiral N-C Bonds (2007)
  • Author(s): K.Kamikawa, K.Nishino, T.Sakamoto, S.Kinoshita, H.Matsuzaka, M.Uemura
  • Journal Title: J, Org.Chem 72 Pages: 3394-3402
  • Peer Reviewed
• [Presentation] アレーンクロム錯体の位置選択的リチオ化反応 (2009)
  • Author(s): 村井真人、上西潤一、植村元一
  • Organizer: 日本薬学会129年会
  • Place of Presentation: 京都国際会館
  • Year and Date: 2009-03-27
• [Presentation] アレーンクロム錯体の位置選択的リチオ化反応 (2009)
  • Author(s): 村井真人, 上西潤一, 植村元一
  • Organizer: 日本薬学会
  • Place of Presentation: 京都国際会館
  • Year and Date: 2009-03-27
• [Presentation] アレーンクロム錯体の位置選択的リチオ化反応 (2008)
  • Author(s): 村井真人、上西潤一、植村元一
  • Organizer: 第58回日本薬学会近畿支部
  • Place of Presentation: 神戸薬科大学
  • Year and Date: 2008-10-25