Development of highly selective synthetic methodology using axially chiral amine organocatalysts

• Project/Area Number: 20750030
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Kyoto University
• Principal Investigator: KANO Taichi Kyoto University, 大学院・理学研究科, 講師 (40372560)
• Project Period (FY): 2008 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2008: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 有機触媒 / 不斉合成 / 有機分子触媒 / 不斉触媒 / アミノオキシル化 / マンニッヒ反応

Research Abstract

Recently various chiral amines derived from natural amino acids are utilized in asymmetric synthesis as catalyst. In our research, novel chiral amine catalysts, which are not derived from natural compounds such as amino acids, were developed, and various reactions of highly reactive substrates were realized by using their characteristic properties.

Research Products

• [Journal Article] Direct Asymmetric Benzoyloxylation of Aldehydes Catalyzed by 2-Tritylpyrrolidine (2009)
  • Author(s): Kano, T.; Mii, H.; Maruoka, K.
  • Journal Title: J. Am. Chem. Soc. 131 Pages: 3450-3451
• [Journal Article] Organocatalytic Approach to Enantioselective One-Pot Synthesis of Pyrrolidine, Hexahydropyrrolizine, and Octahydroindolizine Core Structures (2009)
  • Author(s): Wang, Y. -G.; Kumano, T.; Kano, T.; Maruoka, K.
  • Journal Title: Org. Lett. 11 Pages: 2027-2029
• [Journal Article] Rate Enhancement of Phase Transfer Catalyzed Conjugate Additions by CsCl (2009)
  • Author(s): Kano, T.; Kumano, T.; Maruoka, K.
  • Journal Title: Org. Lett. 11 Pages: 2023-2025
• [Journal Article] Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Mannich Reactions of N-Boc-protected Imines (2009)
  • Author(s): Kano, T.; Yamaguchi, Y.; Maruoka K.
  • Journal Title: Angew. Chem., Int. Ed. 48 Pages: 1838-1840
• [Journal Article] Catalytic Enantioselective Construction of All-carbon Quaternary Stereocenters by an Organocatalytic Diels-Alder Reaction of α-Substituted α, β-Unsaturated Aldehydes (2009)
  • Author(s): Kano, T.; Tanaka, Y.; Osawa, K.; Yurino, T.; Maruoka, K.
  • Journal Title: Chem. Commun. Pages: 1956-1958
• [Journal Article] A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric anti-Selective Mannich Reactions and syn-Selective Cross-Aldol Reactions (2009)
  • Author(s): Kano, T.; Yamaguchi, Y.; Maruoka K.
  • Journal Title: Chemistry-A European Journal 15 Pages: 6678-6687
  • Peer Reviewed
• [Journal Article] Rate Enhancement of Phase Transfer Catalyzed Conjugate Additions by CsCl (2009)
  • Author(s): Kano, T.; Kumano, T.; Maruoka
  • Journal Title: Organic Letters 11 Pages: 2023-2025
  • Peer Reviewed
• [Journal Article] Organocatalytic Approach to Enantioselective One-Pot Synthesis of Pyrrolidine, Hexahydropyrrolizine, and Octahydroindolizine Core Structures (2009)
  • Author(s): Wang, Y.-G.; Kumano, T.; Kano, T.; Maruoka, K.
  • Journal Title: Organic Letters 11 Pages: 2027-2029
  • Peer Reviewed
• [Journal Article] Catalytic Enantioselective Construction of All-carbon Quaternary Stereocenters by an Organocatalytic Diels-Alder Reaction of α-Substituted α,β-Unsaturated Aldehydes (2009)
  • Author(s): Kano, T.; Tanaka, Y.; Osawa, K.; Yurino, T.; Maruoka, K.
  • Journal Title: Chemical Communications Pages: 1956-1958
  • Peer Reviewed
• [Journal Article] Direct Asymmetric Benzoyloxylation of Aldehydes Catelyzd by 2-Trityloyrrolidine (2009)
  • Author(s): Kano, T.; Mii, II. ; Maruoka, K.
  • Journal Title: Journal of the American Chemical Society 131(印刷中)
  • Peer Reviewed
• [Journal Article] Design of Chiral Bifunctional Secondary Amine Catalysts for Asymmetric Enamine Catalysis (2009)
  • Author(s): Kano, T. ; Maruoka, K.
  • Journal Title: Chemical Communications 48 Pages: 1838-1840
  • Peer Reviewed
• [Journal Article] Facile Synthesis of Structurally Diverse 3, 3'-Disubstituted 1, 1'-Binaphthyl-2, 2' -Diamines in Optically Pure Forms (2008)
  • Author(s): Kano, T.; Tanaka, Y.; Osawa, K.; Yurino, T.; Maruoka, K.
  • Journal Title: J. Org. Chem. 73 Pages: 7387-7389
• [Journal Article] Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Mannich Reactions of N-Boc-protected Imines (2008)
  • Author(s): Kano, T. ; Yamaguchi, Y. ; Maruoka, K.
  • Journal Title: Angewandtc Chemie International Edition Pages: 5465-5473
  • Peer Reviewed
• [Journal Article] Facile Synthesis of Structurally Diverse 3, 3' -Disubstituted 1, 1'-Binaphthy1-2, 2'-Diamines in Optically Pure Forms (2008)
  • Author(s): Kano, T.: Tanaka, Y.: Osawa, K. ; Yurino, T. ; Maruoka, K.
  • Journal Title: The Journal of Organic Chemistry 73 Pages: 7387-7389
  • Peer Reviewed
• [Journal Article] Direct Asymmetric Aminoxylation Reaction Catalyzed by a Binaphthyl-based Chiral Amino Sulfonamide with High Catalytic Performance (2008)
  • Author(s): Kano, T.; Yamamoto, A. ; Maruoka, K.
  • Journal Title: Tetrahedron Letters 49 Pages: 5369-5371
  • Peer Reviewed
• [Journal Article] Direct Asymmetric Aminoxylation Reaction Catalyzed by Axially Chiral Amino Acids (2008)
  • Author(s): Kano, T. ; Yamamoto, A.; Mii, H. ; Takai, Shirakawa, S. ; Maruoka, K.
  • Journal Title: Chemistry Letters 37 Pages: 250-251
  • NAID: 10021077999
  • Peer Reviewed
• [Presentation] ビナフチル型アミン触媒を用いた直截的不斉アミノオキシル化反応の開発 (2010)
  • Author(s): 三井晴可、加納太一、丸岡啓二
  • Organizer: 日本化学会90春季年会
  • Place of Presentation: 近畿大学(大阪)
• [Presentation] ビナフチル型アミン触媒を用いた直截的不斉臭素化反応の開発 (2010)
  • Author(s): 白水文貴、加納太一、丸岡啓二
  • Organizer: 日本化学会90春季年会
  • Place of Presentation: 近畿大学(大阪)
• [Presentation] 2-トリチルピロリジン触媒を用いた直截的不斉ベンゾイロキシル化反応の開発 (2009)
  • Author(s): 三井晴可、加納太一、丸岡啓二
  • Organizer: 日本化学会89春季年会
  • Place of Presentation: 日本大学(千葉)
• [Presentation] ビナフチル型アミノスルホンアミド触媒を用いた直截的不斉Mannich反応の開発 (2009)
  • Author(s): 山口祐賀子、加納太一、丸岡啓二
  • Organizer: 日本化学会89春季年会
  • Place of Presentation: 日本大学(千葉)
• [Presentation] 塩化セシウムの添加による相間移動条件下での共役付加反応の加速化:有機分子触媒を用いるピロリジン誘導体の効率的不斉合成 (2009)
  • Author(s): 熊野岳、加納太一、丸岡啓二
  • Organizer: 日本化学会89春季年会
  • Place of Presentation: 日本大学(千葉)
• [Presentation] Enantioselective 1, 3-Dipolar Cycloaddition Reaction between Diazoacetates and α-Substituted Acroleins: Total Synthesis of Manzacidin A (2008)
  • Author(s): 加納太一、橋本卓也、丸岡啓二
  • Organizer: The 23rd International Conferences on Organometallic Chemistry
  • Place of Presentation: レンヌ大学(フランス)
• [Presentation] Enantioselective 1, 3-Dipolar Cycloaddition Reaction between Diazoacetates and α-Substituted Acroleins : Total Synthesis of Manzacidin A (2008)
  • Author(s): 加納太一
  • Organizer: The 23rd International Conferences on Organometallic Chemistry
  • Place of Presentation: Rennes
• [Remarks] ホームページ等