Development of high active artificial nanozymes for enantioselective reactions

2011 Fiscal Year Final Research Report

• Project/Area Number: 22790010
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Osaka University
• Principal Investigator: TAKIZAWA Shinobu 大阪大学, 産業科学研究所, 准教授 (50324851)
• Co-Investigator(Renkei-kenkyūsha): SASAI Hiroaki 大阪大学, 産業科学研究所, 教授 (90205831)
• Project Period (FY): 2010 – 2011
• Keywords: 不斉触媒 / ナノ粒子 / 光学活性 / 環境調和型プロセス / トリアゾール / ドミノ反応 / aza-MBH反応 / RC反応

Research Abstract

Towards the construction of artificial nanozymes for enantioselective reactions, new chiral catalysts for the aza-MBH and the RC reaction, and spiro bis(1, 2, 3-triazolium) salts as room temperature ionic liquids have been developed.

Research Products

• [Journal Article] Enantioselective synthesis ofα-alkylidene-γ-butyrolactones via an intramolecular Rauhut-Currier reaction promoted by acid-base organocatalysts (2012)
  • Author(s): 滝澤忍、T. M.-N. Nguyen、A. Grossmann、D. Enders、笹井宏明
  • Journal Title: Angew. Chem. Int. Ed. Volume: Vol.51(in press)
  • DOI: DOI:10.1002/anie.201201542
  • Peer Reviewed
• [Journal Article] Synthesis of spiro bis(1, 2, 3-triazolium) salts as chiral ionic liquids (2011)
  • Author(s): 吉田泰志、滝澤忍、笹井宏明
  • Journal Title: Tetrahedron Lett. Volume: Vol.52 Pages: 6877-6879
  • DOI: DOI:10.1016/j.tetlet.2011.09.152
  • Peer Reviewed
• [Journal Article] Bifunctional spiro-type organocatalyst with high enantiocontrol : Application to the aza-Morita-Baylis-Hillman reactions (2011)
  • Author(s): 滝澤忍、桐山貴美子、家喜健太、笹井宏明
  • Journal Title: Chem. Commun. Volume: Vol.47 Pages: 9227-9229
  • DOI: DOI:10.1039/C1CC12784E
  • Peer Reviewed
• [Journal Article] An enantioselective organocatalyzed aza-MBH domino process : application to the facile synthesis of tetrahydropyridines (2011)
  • Author(s): 滝澤忍、井上直人、笹井宏明
  • Journal Title: Tetrahedron Lett. Volume: Vol.52 Pages: 377-380
  • DOI: DOI:10.1016/j.tetlet.2010.11.045
  • Peer Reviewed
• [Journal Article] Enantioselective synthesis of isoindolines : Organocatalyzed domino process based on the aza-Morita-Baylis-Hillman(aza-MBH) reaction (2010)
  • Author(s): 滝澤忍、井上直人、平田修一、笹井宏明
  • Journal Title: Angew. Chem. Int. Ed. Volume: Vol.49 Pages: 9725-9729
  • DOI: DOI:10.1002/anie.201004547
  • Peer Reviewed
• [Journal Article] Acid-base organocatalysts for aza-Morita-Baylis-Hillman reaction of nitroalkenes (2010)
  • Author(s): 滝澤忍、堀井厚志、笹井宏明
  • Journal Title: Tetrahedron : Asymmetry Volume: Vol.21 Pages: 891-894
  • DOI: DOI:10.1016/j.tetasy.2010.05.027
  • Peer Reviewed
• [Presentation] Enantioselective C-C bond-forming reactions using vanadium(V) complexes (2012)
  • Author(s): 滝澤忍、小寺純平、Doss Rajesh、片山智美、笹井宏明
  • Organizer: 243rd ACS National Meeting
  • Place of Presentation: San Diego(USA)
  • Year and Date: 2012-03-26
• [Presentation] Organocatalyzed domino process based on the aza-Morita-Baylis-Hillman(aza-MBH) reaction (2011)
  • Author(s): 滝澤忍、平田修一、井上直人、笹井宏明
  • Organizer: ICCEOCA-6
  • Place of Presentation: 香港(中国)
  • Year and Date: 2011-12-12
• [Presentation] Organocatalyzed domino process based on the aza-Morita-Baylis-Hillman(aza-MBH) reaction (2011)
  • Author(s): 平田修一、滝澤忍、井上直人、笹井宏明
  • Organizer: The 1st Junior International Conference on Cutting-Edge Organic Chemistry in Asia
  • Place of Presentation: 廈門(中国)
  • Year and Date: 2011-12-09
• [Presentation] Enantioselective carbon-carbon bond-forming reactions using vanadium(V) complexes (2011)
  • Author(s): 滝澤忍、小寺純平、Doss Rajesh、片山智美、笹井宏明
  • Organizer: Aachen-Osaka Mini-Symposium
  • Place of Presentation: Aachen(Germany)
  • Year and Date: 2011-09-01
• [Presentation] Development of bifunctional organocatalysts for enantioselective Morita-Baylis-Hillman reaction (2010)
  • Author(s): 村上真耶、滝澤忍、笹井宏明
  • Organizer: Pacifichem2010
  • Place of Presentation: Hawaii(USA)
  • Year and Date: 2010-12-17
• [Presentation] Enantioselective aza-Morita-Baylis-Hillman(aza-MBH) domino reactions promoted by acid-base organocatalyst (2010)
  • Author(s): 井上直人、滝澤忍、笹井宏明
  • Organizer: Pacifichem2010
  • Place of Presentation: Hawaii(USA)
  • Year and Date: 2010-12-17
• [Presentation] Bifunctional organocatalyst bearing(S)-1, 1'-spirobiindane as chiral backbone (2010)
  • Author(s): 桐山貴美子、滝澤忍、笹井宏明
  • Organizer: Pacifichem2010
  • Place of Presentation: Hawaii(USA)
  • Year and Date: 2010-12-17
• [Presentation] Enantioselective oxidative coupling of 2-naphthols using dinuclear vanadium complex (2010)
  • Author(s): 滝澤忍、片山智美、Doss Rajesh、笹井宏明
  • Organizer: Pacifichem2010
  • Place of Presentation: Hawaii(USA)
  • Year and Date: 2010-12-16
• [Book] Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis, Chapter 10 : Immobilization of Multicomponent Asymmetric Catalysts(MACs) (2011)
  • Author(s): 笹井宏明、滝澤忍
  • Total Pages: 293-322
  • Publisher: John Wiley & Sons, Inc.
• [Remarks]
  • URL: http://www.sanken.osaka-u.ac.jp/labs/soc/socmain.html
• [Patent(Industrial Property Rights)] 光学活性スピロビストリアゾール誘導体の開発と応用 (2011)
  • Inventor(s): 笹井宏明、滝澤忍、吉田泰志
  • Industrial Property Rights Holder: 大阪大学
  • Industrial Property Number: 特許、特願2011-053422号
  • Filing Date: 2011-03-10