Stereoselective synthesis of chiral-at metal complexes and their asymmetric catalysis

• Project/Area Number: 22750095
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: Kyushu University
• Principal Investigator: MATSUMOTO Kazuhiro 九州大学, 大学院・理学研究院, 助教 (40512182)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000); Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2010: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
• Keywords: 有機合成 / 不斉反応 / 合成化学 / 酸化反応

Research Abstract

The objective of this research is stereoselective synthesis of chiral-at-metal complexes and the development of their asymmetric catalysis. High enantioselectivity has been achieved in the following three asymmetric reactions: titanium-catalyzed asymmetric epoxidation of enol esters, aluminum-catalyzed asymmetric oxidation of thioacetals, and vanadium-catalyzed asymmetric synthesis of non-protected cyanohydrins

Research Products

• [Journal Article] Asymmetric epoxidation of (Z)-enol esters catalyzed by titanium (salalen) complex with aqueous hydrogen peroxide (2011)
  • Author(s): 松本和弘、馮超、半田聡、小熊卓也、香月勗
  • Journal Title: Tetrahedron Volume: 67 Issue: 35 Pages: 6474-6478
  • DOI: 10.1016/j.tet.2011.06.022
  • Peer Reviewed
• [Journal Article] Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids-first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (-)-trans-dihydroxygirinimbine (2011)
  • Author(s): Konstanze K. Gruner, Thomas Hopfmann, Kazuhiro Matsumoto, Anne Jager, Tsutomu Katsuki and Hans-Joachim Knolke
  • Journal Title: Organic and Biomolecular Chemistry Volume: Vol.9、No.7 Issue: 7 Pages: 2057-2061
  • DOI: 10.1039/c0ob01088j
  • Peer Reviewed
• [Journal Article] Catalytic Asymmetric Oxidation of Cyclic Dithioacetals: Highly Diastereo- and Enantioselective Synthesis of the S-Oxides by a Chiral Aluminum(salalen) Complex (2011)
  • Author(s): unichi Fujisaki, Kenji Matsumoto, Kazuhiro Matsumoto and Tsutomu Katsuki
  • Journal Title: Journal of American Chemical Society Volume: Vol.133、No.1 Issue: 1 Pages: 56-61
  • DOI: 10.1021/ja106877x
  • Peer Reviewed
• [Journal Article] Catalytic Asymmetric Oxidation of Cyclic Dithioacetals : Highly… (2011)
  • Author(s): J.Fujisaki, et al
  • Journal Title: Journal of the American Chemical Society Volume: 133 Pages: 56-61
  • Peer Reviewed
• [Journal Article] Room-temperature synthesis of Enantioenriched non-protected cyanohydrins using vanadium(salalen) catalyst (2010)
  • Author(s): Yoshifumi Sakai, Junko Mitote, Kazuhiro Matsumoto and Tsutomu Katsuki
  • Journal Title: Chemical Communication Volume: Vol.46 Issue: 31 Pages: 5787-5789
  • DOI: 10.1039/c0cc00588f
  • Peer Reviewed
• [Journal Article] Room-temperature synthesis of Enantioenriched non-protected… (2010)
  • Author(s): Y.Sakai, et al
  • Journal Title: Chemical Communications Volume: 46 Pages: 5787-5789
  • Peer Reviewed
• [Presentation] チタン-サラレン触媒を用いた(Z)-エノールエステルの不斉エポキシ化 (2012)
  • Author(s): 松本和弘、馮超、半田聡、小熊卓也、香月勗
  • Organizer: 日本化学会第92春季年会(2012)
  • Place of Presentation: 慶應義塾大学、神奈川
  • Year and Date: 2012-03-26
• [Presentation] チタン-サラレン触媒を用いた(Z)-エノールエステルの不斉エポキシ化反応 (2012)
  • Author(s): 松本和弘、馮超、半田聡、小熊卓也、香月勗
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学(神奈川県)
  • Year and Date: 2012-03-26
• [Presentation] チタン-サラレン触媒を用いた(Z)-エノールエステルの不斉エポキシ化反応 (2011)
  • Author(s): 松本和弘、馮超、半田聡、小熊卓也、香月勗
  • Organizer: 第41回複素環化学討論会
  • Place of Presentation: 祟城大学市民ホール、熊本
  • Year and Date: 2011-10-22
• [Presentation] チタン-サラレン触媒を用いた(Z)-エノールエステルの不斉エポキシ化反応 (2011)
  • Author(s): 松本和弘、馮超、半田聡、小熊卓也、香月勗
  • Organizer: 第41回複素環化学討論会
  • Place of Presentation: 崇城大学市民ホール(熊本県)
  • Year and Date: 2011-10-22
• [Presentation] Development of Chiral Titanium Complexes for Asymmetric Olefin Epoxidation Using Aqueous Hydrogen Peroxide as Oxidant (2011)
  • Author(s): Kazuhiro Matsumoto and Tsutomu Katsuki
  • Organizer: the 2011 International Symposium on Molecular Systems ~Global COE Symposium for Young Researchers~
  • Place of Presentation: ザ・ルイガンズ、福岡
  • Year and Date: 2011-05-10
• [Presentation] Development of Chiral Titanium Complexes for Asymmetric Olefin Epoxidation Using Aqueous Hydrogen Peroxide as Oxidant (2011)
  • Author(s): 松本和弘、香月勗
  • Organizer: the 2011 International Symposium on Molecular Systems ～Global COE Symposium for Young Researchers～
  • Place of Presentation: ザ・ルイガンズ(福岡県)
  • Year and Date: 2011-05-10
• [Presentation] C3対称トリスフェノールアミン錯体のプロペラ型不斉制御と不斉反応への応用 (2011)
  • Author(s): 重永美由希、松本和弘、香月勗
  • Organizer: 日本化学会第91春季年会(2011)
  • Place of Presentation: 神奈川大学、神奈川
  • Year and Date: 2011-03-27
• [Presentation] C_3対称トリスフェノールアミン錯体のプロペラ型不斉制御と不斉反応への応用 (2011)
  • Author(s): 重永美由希、松本和弘、香月勗
  • Organizer: 日本化学会第91回春季年会
  • Place of Presentation: 神奈川大学(神奈川県)
  • Year and Date: 2011-03-27
• [Presentation] バナジウム-サラレン錯体を触媒として用いた無保護シアノヒドリンの高エナンチオ選択的合成法の開発 (2011)
  • Author(s): 松本和弘、境芳郁、三戸手順子、香月勗
  • Organizer: 日本化学会第91春季年会(2011)
  • Place of Presentation: 神奈川大学、神奈川
  • Year and Date: 2011-03-26
• [Presentation] バナジウム-サラレン錯体を触媒として用いた無保護シアノヒドリンの (2011)
  • Author(s): 松本和弘、境芳郁、香月勗
  • Organizer: 日本化学会第91回春季年会
  • Place of Presentation: 神奈川大学(神奈川県)
  • Year and Date: 2011-03-26
• [Presentation] バナジウム-サラレン錯体を触媒として用いた無保護シアノヒドリンの高エナンチオ選択的合成法の開発 (2010)
  • Author(s): 松本和弘、境芳郁、三戸手順子、香月勗
  • Organizer: 第98回有機合成シンポジウム
  • Place of Presentation: 早稲田大学国際会議場
  • Year and Date: 2010-11-05
• [Presentation] バナジウム錯体を用いた室温における無保護シアノヒドリンの高エナンチオ (2010)
  • Author(s): 松本和弘、境芳郁、香月勗
  • Organizer: 第98回有機合成シンポジウム
  • Place of Presentation: 早稲田大学国際会議場
  • Year and Date: 2010-11-05
• [Book] Comprehensive Chirality Vol. 5 ISBN: 978-0-08-095168-3 (2012)
  • Author(s): Kazuhiro Matsumoto and Tsutomu Katsuki
• [Book] 5.3 Oxidation: Epoxidation (Allylic Alcohol, Homoallylic Alcohol, Simple C=C, Electron Deficient C=C), in Comprehensive Chirality, Vol. 5 (2012)
  • Author(s): Kazuhiro Matsumoto and Tsutomu Katsuki
  • Publisher: Elsevier