Development of evaluation method for configurational stability of chiral carbanions

• Project/Area Number: 21890151
• Research Category: Grant-in-Aid for Research Activity Start-up
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Hiroshima University
• Principal Investigator: IKEMOTO Hidaka Hiroshima University, 大学院・医歯薬学総合研究科, 助手 (60549004)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥2,652,000 (Direct Cost: ¥2,040,000、Indirect Cost: ¥612,000); Fiscal Year 2010: ¥1,261,000 (Direct Cost: ¥970,000、Indirect Cost: ¥291,000); Fiscal Year 2009: ¥1,391,000 (Direct Cost: ¥1,070,000、Indirect Cost: ¥321,000)
• Keywords: 合成化学 / 不斉反応 / キラルカルバニオン / 立体化学的安定性 / Wittig転位 / 溶媒効果 / 求電子置換反応

Research Abstract

We have developed a new method for quantitatively assessing the configurational stability of organolithiums next to conjugative electron-withdrawing group in which the stability can be estimated from the stereochemical analysis of the products in the reaction. We have also examined the effects of solvents on the configurational stability of chiral carbanions using a variety of solvents and additives.

Research Products

• [Journal Article] Solvent Effects on the Steric Course of [2,3]-Wittig Rearrangement of (S,E)-(3-(allyloxy) prop-1-ene-1,3-diyl) diben zene and Its Derivatives. (2011)
  • Author(s): 池本陽峰, 佐々木道子, 武田敬
  • Journal Title: Eur.J.Org.Chem. Pages: 6643-6650
  • Peer Reviewed
• [Journal Article] キラルカルバニオンの化学-"オモテ"と"ウラ"の話- (2010)
  • Author(s): 佐々木道子, 池本陽峰, 武田敬
  • Journal Title: 月刊化学(最新のトピックス(化学同人)) 6月号 Pages: 66-67
  • Peer Reviewed
• [Journal Article] Solvent Effects on the Steric Course of [2,3]-Wittig Rearrangement of (S,E)-(3-(allyloxy)prop-1-ene-1,3-diyl)dibenzene and Its Derivatives (2010)
  • Author(s): Hidaka Ikemoto
  • Journal Title: European Journal of Organic Chemistry Pages: 6643-6650
  • Peer Reviewed
• [Journal Article] Development of Epoxysilane Rearrangement and its Application to Chirality Transfer. (2009)
  • Author(s): M, Sasaki.H, Ikemoto.K, Takeda
  • Journal Title: Heterocycles 78 Pages: 2919-2941
  • NAID: 40016842003
  • Peer Reviewed
• [Journal Article] [2,3]-Wittig Rearrangement of Enantiomerically Enriched 3-Substituted 1-Propenyloxy-1-phenyl-2-propen-1-yl Carbanions : Effect of Heteroatoms and Conjugating Groups on Planarization of an a-Oxy-Benzylcarbanion Through a Double Bond. (2009)
  • Author(s): M, Sasaki.H, Ikemoto.M, Kawahata. K, Yamaguchi. K, Takeda
  • Journal Title: Eur.J.Org.Chem. 15 Pages: 4663-4666
  • Peer Reviewed
• [Journal Article] [2, 3]-Wittig Rearrangement of Enantiomerically Enriched 3-Substituted 1-Propenyloxy-1-phenyl-2-propen-1-yl Carbanions : Effect of Heteroatoms and Conjugating Groups on Planarization of an α-Oxy-Benzylcarbanion Through a Double Bond (2009)
  • Author(s): Michiko Sasaki
  • Journal Title: Chemistry-A European Journal 15 Pages: 4663-4666
  • Peer Reviewed
• [Journal Article] Development of Epoxysilane Rearrangement and its Application to Chirality Transfer (2009)
  • Author(s): Michiko Sasaki
  • Journal Title: Heterocycles 78 Pages: 2919-2941
  • Peer Reviewed
• [Presentation] キラルカルハ・ニオンの立体特異的な求電子反応を利用するL-アミノ酸誘導体の不斉アルキル化 (2011)
  • Author(s): 池本陽峰, 佐々木道子, 武田敬
  • Organizer: 日本薬学会第131年会
  • Place of Presentation: 静岡
  • Year and Date: 2011-03-31
• [Presentation] キラルカルバニオンの立体特異的な求電子反応を利用するL-アミノ酸誘導体の不斉アルキル化 (2011)
  • Author(s): 池本陽峰
  • Organizer: 日本薬学会第131年会
  • Place of Presentation: 静岡市
  • Year and Date: 2011-03-31
• [Presentation] 共役性電子求引基に隣接するキラルカルバニオンの立体化学的安定性の評価法の開発 (2010)
  • Author(s): 佐々木道子, 藤原美智, 池本陽峰, 武田敬
  • Organizer: 第49回日本薬学会・日本病院薬剤師会中国四国支部学術大会
  • Place of Presentation: 鳥取
  • Year and Date: 2010-11-06
• [Presentation] キラルα-ニトリルカルバニオンの発生と求電子剤による捕捉 (2010)
  • Author(s): 佐々木道子, 竹川友, 池本陽峰, 武田敬
  • Organizer: 第49回日本薬学会・日本病院薬剤師会中国四国支部学術大会
  • Place of Presentation: 鳥取
  • Year and Date: 2010-11-06
• [Presentation] 共役性電子求引基に隣接するキラルカルバニオンの立体化学的安定性の評価法の開発 (2010)
  • Author(s): 池本陽峰
  • Organizer: 第49回日本薬学会・日本病院薬剤師会中国四国支部学術大会
  • Place of Presentation: 米子,鳥取
  • Year and Date: 2010-11-06
• [Presentation] キラルα-ニトリルカルバニオンの発生と求電子剤による捕捉 (2010)
  • Author(s): 池本陽峰
  • Organizer: 第49回日本薬学会・日本病院薬剤師会中国四国支部学術大会
  • Place of Presentation: 米子,鳥取
  • Year and Date: 2010-11-06
• [Presentation] キラルカルバニオンの立体化学的安定性と求電子剤との反応における立体化学 (2010)
  • Author(s): 池本陽峰, 佐々木道子, 藤原美智, 竹川友, 武田敬
  • Organizer: 第36回反応と合成の進歩シンポジウム
  • Place of Presentation: 名古屋
  • Year and Date: 2010-11-02
• [Presentation] キラルカルバニオンの立体化学的安定性と求電子剤との反応における立体化学 (2010)
  • Author(s): 池本陽峰
  • Organizer: 第36回反応と合成の進歩シンポジウム
  • Place of Presentation: 名古屋,愛知
  • Year and Date: 2010-11-01
• [Presentation] [2,3]-Wittig転位を利用するキラルカルバニオンの立体化学的安定性の評価 (2010)
  • Author(s): 池本陽峰, 佐々木道子, 武田敬
  • Organizer: 第7回次世代を担う有機化学シンポジウム
  • Place of Presentation: 大阪
  • Year and Date: 2010-07-23
• [Presentation] Solvent Effects on the Configurational Stability of Chiral Carbanions (2010)
  • Author(s): 池本陽峰, 藤原美智, 武田敬
  • Organizer: 22nd International Symposium on Chirality [Chirality 2010 ; ISCD-22]
  • Place of Presentation: Sapporo, Japan
  • Year and Date: 2010-07-14
• [Presentation] Solvent Effects on the Configurational Stability of Chiral Carbanions (2010)
  • Author(s): 池本陽峰
  • Organizer: 22nd International Symposium on Chirality
  • Place of Presentation: 札幌,北海道
  • Year and Date: 2010-07-14
• [Presentation] キラルカルバニオンの立体化学的安定性に対する溶媒効果 (2010)
  • Author(s): 池本陽峰, 佐々木道子, 武田敬
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
  • Year and Date: 2010-03-29
• [Presentation] キラルカルバニオンの立体化学的安定性に対する溶媒効果 (2010)
  • Author(s): 池本陽峰
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山市
  • Year and Date: 2010-03-29
• [Presentation] Effects of Solvents on the Trapping of Chiral Carbanions by [2,3]-Wittig Rearrangement (2009)
  • Author(s): 池本陽峰, 藤原美智, 武田敬
  • Organizer: 11th International Kyoto Conference on New Aspects of Organic Chemistry [IKCOC-11]
  • Place of Presentation: Kyoto, Japan
  • Year and Date: 2009-11-10
• [Presentation] Effects of Solvents on the Trapping of Chiral Carbanions by [2, 3]-Wittig Rearrangement (2009)
  • Author(s): 池本陽峰
  • Organizer: 11th International Kyoto Conference on New Aspects of Organic Chemistry
  • Place of Presentation: 京都市
  • Year and Date: 2009-11-10
• [Presentation] [2, 3]-Wittig 転位を利用するキラルカルバニオンの立体化学的安定性の評価 (2009)
  • Author(s): 池本陽峰
  • Organizer: 第7回次世代を担う有機合成化学シンポジウム
  • Place of Presentation: 吹田市
  • Year and Date: 2009-07-23
• [Presentation] Trapping of Chiral Carbanions by [2,3]-Wittig Rearrangement : Effect of Heteroatoms and Conjugating Groups (2009)
  • Author(s): 池本陽峰, 藤原美智, 武田敬
  • Organizer: 41st National Organic Chemistry Symposium, the University of Colorado
  • Place of Presentation: Boulder, CO, USA
  • Year and Date: 2009-06-08
• [Presentation] Trapping of Chiral Carbanions by [2, 3]-Wittig Rearrangement : Effect of Heteroatoms and Conjugating Groups (2009)
  • Author(s): 池本陽峰
  • Organizer: 41st National Organic Chemistry Symposimn
  • Place of Presentation: Boulder, CO, USA
  • Year and Date: 2009-06-08
• [Remarks] ホームページ等
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