• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to project page

2011 Fiscal Year Final Research Report

Asymmetric Addition of carbon, nitrogen, oxygen and sulfur nucleophiles and its application to the synthesis of biologically active compounds

Research Project

  • PDF
Project/Area Number 20249002
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionDoshisha Women's College of Liberal Arts (2011)
Kyoto University (2008-2010)

Principal Investigator

TOMIOKA Kiyoshi  同志社女子大学, 薬学部, 教授 (50114575)

Co-Investigator(Renkei-kenkyūsha) YAMADA Ken-ichi  京都大学, 薬学研究科, 准教授 (00335184)
YAMAMOTO Yasutomo  同志社女子大学, 薬学部, 助教 (10452278)
Project Period (FY) 2008 – 2011
Keywords四大元素 / キラル配位子 / 不斉触媒 / 天然物合成 / 連続反応
Research Abstract

Most chiral carbon centers of biologically active compound directly connect to representative 4 atoms, carbon, nitrogen, oxygen, and sulfur atoms. Asymmetric addition reaction of these 4 atoms develops the methodology for the efficient synthesis of useful medicines and biologically active molecules. We achieved asymmetric addition of organolithiums, lithium enolates, lithium amides, organoboranes, organomagnesiums, and organozincs. Asymmetric total synthesis of some natural products was also achieved by using our developed asymmetric reaction as a key step.

  • Research Products

    (27 results)

All 2012 2011 2010 2009 2008

All Journal Article (20 results) Presentation (6 results) Book (1 results)

  • [Journal Article] Steric Influence of N-Phosphorus-arylimines on the Rhodium-Catalyzed Asymmetric Arylation2011

    • Author(s)
      Hao, X.; Chen, Q.; Yamada, K.; Yamamoto, Y.; Tomioka, K
    • Journal Title

      Tetrahedron

      Volume: 67(35) Pages: 6469-6473

    • DOI

      DOI:10.1016/j.tet.2012.03.107

  • [Journal Article] Chiral N-Heterocyclic Carbene. Copper(I)-Catalyzed Asymmetric Allylic Arylation of Aliphatic Allylic Bromides : Steric and Electronic Effects on γ-Selectivity2011

    • Author(s)
      Selim, K. B.; Nakanishi, H.; Matsumoto, Y.; Yamamoto, Y.; Yamada, K.; Tomioka, K
    • Journal Title

      J. Org. Chem

      Volume: 76(5) Pages: 1398-1408

    • DOI

      DOI:10.1021/jo102386s

  • [Journal Article] Rhodium-Catalyzed Asymmetric Phenylation of N-Phosphinoylarylimines with Triphenylborane2011

    • Author(s)
      Hao, X.; Chen, Q.; Kuriyama, M.; Yamada, K.; Yamamoto, Y.; Tomioka, K
    • Journal Title

      Catal. Sci. Tech

      Volume: 1(1) Pages: 62-64

    • DOI

      DOI:10.1039/c0cy00083c

  • [Journal Article] Stereoselective Formal Synthesis of(+)-Allokainic Acid via Thiol-Mediated Acyl Radical Cyclization2010

    • Author(s)
      Yamada, K.; Sato, T.; Hosoi, M.; Yamamoto, Y.; Tomioka, K
    • Journal Title

      Chem. Pharm. Bull

      Volume: 58(11) Pages: 1511-1516

    • DOI

      DOI:10.1248/cpb.58.1511

  • [Journal Article] Stereoselective Radical Addition of an Acetal to Sterically Tuned Enantiomerically Pure N-Sulfinyl Imines2010

    • Author(s)
      Akindele, T.; Yamada, K.; Sejima, T.; Maekawa, M.; Yamamoto, Y.; Nakano, M.; Tomioka, K
    • Journal Title

      Chem. Pharm. Bull

      Volume: 58(2) Pages: 265-269

    • DOI

      DOI:10.1248/cpb.58.265

  • [Journal Article] Chiral Carbene Approach to Gold-Catalyzed Asymmetric Cyclization of 1, 6-Enynes2010

    • Author(s)
      Matsumoto, Y.; Selim, K. B.; Nakanishi, H.; Yamada, K.; Yamamoto, Y.; Tomioka, K
    • Journal Title

      Tetrahedron Lett

      Volume: 51(2) Pages: 404-406

    • DOI

      DOI:10.1016/j.tetlet.2009.11.039

  • [Journal Article] Efficient Chiral N-Heterocyclic Carbene/Copper(I)-Catalyzed Asymmetric Allylic Arylation with Aryl Grignard Reagents2009

    • Author(s)
      Selim, K. B, Matsumoto, Y.; Yamada, K.; Tomioka, K
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 48(46) Pages: 8733-8735

    • DOI

      DOI:10.1002/anie.200904676

  • [Journal Article] Steric Tuning of the Amidomonophosphane-Rhodium(I) Catalyst in Asymmetric Addition of Arylboroxines to N-Phosphinoyl Aldimines2009

    • Author(s)
      Hao, X.; Kuriyama, M.; Chen, Q.; Yamamoto, Y.; Yamada, K.; Tomioka, K
    • Journal Title

      Org. Lett.

      Volume: 11(19) Pages: 4470-4473

    • DOI

      DOI:10.1021/ol901866y

  • [Journal Article] Iron Chloride Enhancement of Dimethylzinc-Mediated Radical Conjugate Addition of Ethers and an Amine to Alkylidenemalonates2009

    • Author(s)
      Yamada, K.; Maekawa, M.; Yamamoto, Y.; Nakano, M.; Akindele, T.; Tomioka, K
    • Journal Title

      Tetrahedron Lett

      Volume: 50(44) Pages: 6040-6043

    • DOI

      DOI:10.1016/j.tetlet.2009.08.034

  • [Journal Article] Chiral Amidophosphane-Rhodium(I)-Catalyzed Asymmetric Conjugate Arylation of Acyclic Enones with Arylboronic Acids2009

    • Author(s)
      Chen, Q.; Kuriyama, M.; Hao, X.; Soeta, T.; Yamamoto, Y.; Yamada, K.; Tomioka, K
    • Journal Title

      Chem. Pharm. Bull

      Volume: 57(9) Pages: 1024-1027

    • DOI

      DOI:10.1248/cpb.57.1024

  • [Journal Article] Asymmetric Construction of Three Contiguous Stereogenic Centers by Conjugate Addition-Alkylation of Lithium Ester Enolate2009

    • Author(s)
      Yamamoto, Y.; Yasuda, Y.; Nasu, H.; Tomioka, K
    • Journal Title

      Org. Lett

      Volume: 11(9) Pages: 2007-2009

    • DOI

      DOI:10.1021/ol900447n

  • [Journal Article] Accessing the Amide Functionality by the Mild and Low-Cost Oxidation of Imine2009

    • Author(s)
      Mohamed, M. A, Yamada, K.; Tomioka, K
    • Journal Title

      Tetrahedron Lett

      Volume: 50(26) Pages: 3436-3438

    • DOI

      DOI:10.1016/j.tetlet.2009.02.174

  • [Journal Article] Total Synthesis of(-)-Lycorine and (-)-2-epi-Lycorine by Asymmetric Conjugate Addition Cascade2009

    • Author(s)
      Yamada, K.; Yamashita, M.; Sumiyoshi, T.; Nishimura, K.; Tomioka, K
    • Journal Title

      Org. Lett

      Volume: 11(7) Pages: 1631-1633

    • DOI

      DOI:10.1021/ol9003564

  • [Journal Article] Dimethylzinc Initiated Radical Reactions2009

    • Author(s)
      Akindele, T, Yamada, K.; Tomioka, K
    • Journal Title

      Acc. Chem. Res

      Volume: 42(2) Pages: 345-355

    • DOI

      DOI:10.1021/ar800166q

  • [Journal Article] Carbon Centers by Sequential Conjugate Addition of Lithium Amide and in situ Alkylation : Utility in the Synthesis of(-)-Aspidospermidine2009

    • Author(s)
      Suzuki, M, Kawamoto, Y.; Sakai, T.; Yamamoto, Y.; Tomioka, K
    • Journal Title

      Org. Lett

      Volume: 11(3) Pages: 653-655

    • DOI

      DOI:10.1021/ol802759j

  • [Journal Article] Tandem Conjugate Addition-Aldol Cyclization of 2-Formylbenzylidenemalonate with Ether Radicals by the Mediation of Dimethylzinc2009

    • Author(s)
      Yamada, K.; Maekawa, M.; Akindele, T.; Yamamoto, Y.; Nakano, M.; Tomioka, K
    • Journal Title

      Tetrahedron

      Volume: 65(4) Pages: 903-908

    • DOI

      DOI:10.1016/j.tet.2008.11.009

  • [Journal Article] Chemoselective Conjugate Addition of Dimethylzinc-Mediated Ether and Acetal Radicals to Alkylidenemalonates and Asymmetric Reactions2008

    • Author(s)
      Yamada, K.; Maekawa, M.; Akindele, T.; Nakano, M.; Yamamoto, Y.; Tomioka, K
    • Journal Title

      Org. Chem

      Volume: 73(24) Pages: 9535-9538

    • DOI

      DOI:10.1021/jo801541m

  • [Journal Article] Copper-Catalyzed Asymmetric Allylic Substitution with Aryl and Ethyl Grignard Reagents2008

    • Author(s)
      Selim, K. B.; Yamada, K.; Tomioka, K.
    • Journal Title

      Chem. Commun

      Volume: (41) Pages: 5140-5142

    • DOI

      DOI:10.1039/b809140d

  • [Journal Article] A Ternary Complex Reagent for An Asymmetric Michael Reaction of Lithium Ester Enolates with Enoates2008

    • Author(s)
      Yamamoto, Y.; Suzuki, H.; Yasuda, Y.; Iida, A.; Tomioka, K
    • Journal Title

      Tetrahedron Lett

      Volume: 49(31) Pages: 4582-4584

    • DOI

      DOI:10.1016/j.tetlet.2008.05.101

  • [Journal Article] Consecutive Cyclization of Allylaminoalkene by Intramolecular Aminolithiation-Carbolithiation2008

    • Author(s)
      Tsuchida, S.; Kaneshige, A.; Ogata, T.; Baba, H.; Yamamoto, Y.; Tomioka, K
    • Journal Title

      Org. Lett

      Volume: 10(16) Pages: 3635-3638

    • DOI

      DOI:10.1021/ol801397v

  • [Presentation] Catalytic Asymmetric Reactions Mediated by Chiral Molecule and Metal2012

    • Author(s)
      Tomioka, K.
    • Organizer
      The 4th Novel Chiral Chemistries Japan
    • Place of Presentation
      東京工業大学くらまえホール(東京都)
    • Year and Date
      2012-03-15
  • [Presentation] Aminolithiation. Carbolithiation Conjugate Process2011

    • Author(s)
      Tomioka, K.
    • Organizer
      ISOR-10
    • Place of Presentation
      慶應大学(神奈川県)
    • Year and Date
      2011-11-23
  • [Presentation] Consecutive aminolithiation. carbolithiation of olefins2010

    • Author(s)
      Tomioka, K.
    • Organizer
      PACIFICHEM2010
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2010-12-16
  • [Presentation] Recent Progress in Dimethylzinc-Initiated Radical Reactions2009

    • Author(s)
      Tomioka, K.
    • Organizer
      The 4th Pacific Symposium on Radical Chemistry
    • Place of Presentation
      Shanghai, China
    • Year and Date
      2009-11-21
  • [Presentation] 二重結合のヒドロアミノ化反応を基軸とする含窒素複素環の合成2008

    • Author(s)
      富岡清
    • Organizer
      有機合成夏期セミナー「明日の有機合成化学」
    • Place of Presentation
      大阪
    • Year and Date
      2008-09-25
  • [Presentation] Hydroamination of Carbon-Carbon Double Bond for Nitrogen-Containing Heterocycles2008

    • Author(s)
      Tomioka, K.
    • Organizer
      ICOS-17
    • Place of Presentation
      Daejeon, Korea
    • Year and Date
      2008-06-25
  • [Book] 化学同人,使える!有機合成反応241実践ガイド2010

    • Author(s)
      富岡清
    • Total Pages
      206-207, 356-357, 436-437, 450-451

URL: 

Published: 2013-07-31  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi