Research on the synthesis of fluorous acylsilanes for the development of environment-conscious organic reaction

• Project/Area Number: 19550103
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Kanazawa University
• Principal Investigator: HONDA Mitsunori Kanazawa University, 物質化学系, 講師 (60242533)
• Co-Investigator(Kenkyū-buntansha): SEGI Masahito 金沢大学, 物質化学系, 教授 (90135046)
• Project Period (FY): 2007 – 2008
• Project Status: Completed (Fiscal Year 2008)
• Budget Amount: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000); Fiscal Year 2008: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000); Fiscal Year 2007: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
• Keywords: 環境調和型反応 / フルオラス合成 / アシルシラン / パーフルオロアルキル基 / アルドール反応 / 細見-櫻井反応 / 細見-桜井反応

Research Abstract

グリーンケミストリーを指向した新しい反応プロセスの開発を目的とし、パーフルオロアルキル基をケイ素原子上に持つアシルシラン類の合成法開発とアシルシランの合成的利用について検討した。その結果、パーフルオロアルキル基を1~3個導入したアセチルシランの合成に成功した。一方、アシルシランのシリル基が持つdirecting group, leaving group としての特異な性質を利用し、不斉中心が連続する炭素鎖の立体選択的な構築法を明らかにした。

Research Products

• [Journal Article] Acid-catalyzed reaction behavior of 1-phenylselenocyclopropylcarbinols (2008)
  • Author(s): Honda, M, Nishizawa, T, Nishii, Y, Segi, M and Nakajima, T
  • Journal Title: Chem. Lett. 37 Pages: 946-947
  • Peer Reviewed
• [Journal Article] Acid-catalyzed reaction behavior of 1-phenylseleno-cyclopropylcarbinols (2008)
  • Author(s): Mitsunori Honda
  • Journal Title: Chemistry Letters 37 Pages: 946-947
  • Peer Reviewed
• [Journal Article] Stereoselective hetero Diels-Alder reaction of selenoaldehydes with pentavalent phosphole chalcogenides (2007)
  • Author(s): Segi, M, Tanno, K, Honda, M and Fujinami, S
  • Journal Title: Tetrahedron Lett. 48 Pages: 3349-3354
  • NAID: 120001133014
  • Peer Reviewed
• [Journal Article] An efficient 1, 3-dipolar cycloaddition between aromatic selenoaldehydes and nitrile oxides or nitrile imines : an easy access to selenium-containing five-membered heterocyclic ring system (2007)
  • Author(s): Segi, M, Kawaai, K, Kojima, M, Honda M and Nakajima, T
  • Journal Title: Tetrahedron Lett. 48 Pages: 2303-2306
  • NAID: 120000809894
  • Peer Reviewed
• [Presentation] [3+2] Cycloaddition reaction of selenoand thio-aldehydes with 1, 3-dipoles (2008)
  • Author(s): Masahito Segi
  • Organizer: The 34th Symposium on Main Group Element Chemistry
  • Place of Presentation: 東京
  • Year and Date: 2008-12-12
• [Presentation] Investuigation of Selenating Reagents for the Direct Conversion of Aldehydes into Selenoaldehydes (2008)
  • Author(s): Masahito Segi
  • Organizer: The 34th Symposium on Main Group Element Chemistry
  • Place of Presentation: 東京
  • Year and Date: 2008-12-12
• [Presentation] [3+2]Cycloaddition reaction of seleno- and thio-aldehydes with 1, 3-dipoles (2008)
  • Author(s): Masahito Segi
  • Organizer: The 34th Symposium on Main Group Element Chemistry
  • Place of Presentation: 東京
  • Year and Date: 2008-12-12
• [Presentation] Acid-catalyzed reaction behavior of 1-silylcyclo-propylcarbinols (2008)
  • Author(s): Mitsunori Honda
  • Organizer: 55th Symposium on Organometallic Chemistry
  • Place of Presentation: 大阪
  • Year and Date: 2008-09-29
• [Presentation] Acid-catalyzed reaction behavior of 1-silylcyclo-propylcarbinols (2008)
  • Author(s): Mitsunori Honda
  • Organizer: 55th Sympos ium on Organometallic Chemistry
  • Place of Presentation: 大阪
  • Year and Date: 2008-09-29
• [Presentation] A New Approach to the Synthesis of 1, 2, 3-Triols Using α, β-Unsaturated Acylsilanes (2007)
  • Author(s): Mitsunori HONDA
  • Organizer: 54th Symposium on Organometallic Chemistry, Japan
  • Place of Presentation: 広島
  • Year and Date: 2007-10-27
• [Presentation] Stereoselective Synthesis of 1, 2, 3-Triols Using α, β-Unsaturated Acylsilanes (2007)
  • Author(s): Mitsunori HONDA
  • Organizer: 14th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
  • Place of Presentation: 奈良
  • Year and Date: 2007-08-03
• [Book] (2008)
  • Author(s): Masahito Segi
  • Total Pages: 74
  • Publisher: Thieme, Science of Synthesis
• [Book] Science of Synthesis (2008)
  • Author(s): Masahito Segi
  • Total Pages: 74
  • Publisher: Thieme
• [Remarks]
  • URL: http://dspace.lib.kanazawa-u.ac.jp/dspace/