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1991 Fiscal Year Final Research Report Summary

Development of New Organic Reactions and Synthesis of Physiologically Active Substance

Research Project

Project/Area Number 62065005
Research Category

Grant-in-Aid for Specially Promoted Research

Allocation TypeSingle-year Grants
Research InstitutionNagoya University

Principal Investigator

NOYORI Ryoji  Nagoya University, Chemistry, Professor Faculty of Science, 理学部, 教授 (50022554)

Co-Investigator(Kenkyū-buntansha) KITAMURA Masato  Nagoya Uni. Fac. of Science Assoc. Professor, 理学部, 助教授 (50169885)
MARUOKA Keiji  Nagoya Uni. Fac. of Engineering Assoc. Professor, 工学部, 助教授 (20135304)
SUZUKI Masaaki  Nagoya Uni., Chemical Instrument Center Assoc. Professor, 化学測定機器センター, 助教授 (90093046)
HAYAKAWA Yoshihiro  Nagoya Uni., College of General Edcation Assoc. Professor, 教養部, 助教授 (50022702)
YAMAMOTO Hisashi  Nagoya Uni., Chemistry, Fac. of Engineering Professor, 工学部, 教授 (10135311)
Project Period (FY) 1987 – 1990
KeywordsBINAL-H / TMSOTf / BINAP / BINAP-Rh / BINAP-Ru / MAD / CAB / Pd(0)Catalyzed deprotection
Research Abstract

Research objectives : the following six objectives have been studied. (1) development of new synthetic organic reactions and management of the research (R. Noyori), (2) development of new reactions based on the use of typical elements (H. Yamamoto), (3) synthesis of oligonucleotides (B. Hayakawa), (4) prostaglandin synthesis (M. Suzuki), (5) synthesis of anthracyclin antibiotics (K. Maruoka), (6) synthesis of alkaloids, terpines, and vitamines (M. Kitamura).
Results : successful results are summarized as follows. (1) organozinc aided stereoselective conjugate addition to enones and selective momoalkylation of enolates ; selective propargylation of carbonyls ; catalysis of PG endoperoxides ; asymmetric reduction of carbonyls with BINAL-H ; TMSOTf catalyzed aldol-type reactions ; practical synthesis of BINAP ; BINAP-Rh catalyzed asymmetric hydrogenation of olefins ; BINAP-Ru (II) catalyzed asymmetric hydrogenation of functionalized olefins ; kinetic resolution of allylic alcohols by BINAP … More -Ru catalyzed hydrogenation ; asymmetric synthesis of diols by double stereodifferentiation ; kinetic resolution of a racemic hydroxy ketones ; assymmetric synthesis using dynamic kinetic resolution ; asymmetric 1, 3-hydrogen shift catalyzed by BINAP-Rh catalyst ; kinetic resolution of 4-hydroxy-2-cyclopentenone ; catalytic enantioselective alkylation using organozinc reagents and elucidation of the mechanism ; efficient Pd(O)-catalyzed deprotection of allyl- and allyloxycarbonyl protective groups in nucleosides and ncleotides ; synthesis of unsymmetrically (2'-5'), (3'-5') linked oligonucleotides. (2) amphiphilic alkylation using alliminium agents, MAD and MAT : synthesis of steroids, conjugate addition of enones, selective reduction of two different ketones ; organoaluminium-promoted Claisen rearrangement : synthesis of Lardolure and Recifeolide ; CAB catalysis in organic synthesis : asymmetric Diels-Alder reaction, Aldol reaction, enereaction ; stereoselective synthesis of geranyl- and neryl-metal reagents ; synthesis of Ubiquinone 10. (3) synthesis of extremely pure 60 mers of oligonucleotides ; direct synthesis of solid-anchored DNA oligomers. (4) extremely shot-step synthesis of prostaglandin E_2 ; general syntheis of PGs ; synthesis of isocarbacyclin, synthesis of punaglandins ; synthesis of a photoaffinity probe reagent for prostacyclin receptor. (5) asymmetric Hetero-Diels-Alder reaction based on the use of binaphthol modified chiral alunminium agent AL ; efficient in situ generation of chiral Lewis acid ; asymmetric ene and Claisen reactions with AL ; stereoselcctive C-glycosidation ; synthesis of pseudosugars ; efficient synthesis of a partial structure of FK506 ; efficient construction of anthracyclin skeletons. (6) BINAP-Ru catalyzed enantioselective hydrogenation of enamides ; synthesis of a key intermediate for general synthesis of isoquinoline alkaloids ; asymmetric hydrogenation of allylic alcohols ; BINAP-Ru catalyzed asymmetric hydrogenation of bifunctionalized ketones ; asymmetric synthesis of 1beta-methylcarbapenems ; asymmetric synthesis of beta-amino acids ; asymmetric synthesis of camitine, statine, and analogues ; stereoselective synthesis of threonine type compounds. Less

  • Research Products

    (31 results)

All Other

All Publications (31 results)

  • [Publications] R.Noyori and M.Suzuki: "An Organometallic way to Prostaglandins:The Three-compcnent conpling Synthesis" Chemtracts-Org.Chem.3. 173-197 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Inoue,H.Takaya,K.Tani,S.Otsuka,T.Sato,and R.Nayori: "Mechanism of the Asyumetric Isomerization of Allylamines to Enamines Catalyzed by 2,2'-Bis (diphenylphosphinc)-1,1'-binaphthyl-Rhodium Complexes" J.Am.Chem.Soc. 112. 4897-4905 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Maruoka,S.Nagahara,and H.Yamaoto: "Molemlar Recugnitron of Ethers with Modified Organoaluinium Reagents" J.Am.Chem.Soc. 112. 6115-6117 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] R.Noyori and H.Takaya: "BINAP:An Efficient Chired Elerent for Asymmetric Catrlgsis" Acc.Chem.Res.23. 345-350 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] R.Noyori and M.Kitamura: "Enantioselective Addition of Organometallic Reagents to Carbongl compounds:Chirality Transter,Multiplication,and Amplitication" Angew.Chem.Int.Ed.Engl.30. 49-69 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Hayakawa,S.Wakabayashi,H.Kato,and R.Nayori: "The Allylic Protection Method in Solid-Phose Oligonicleotide synihesis.An Efficient Preparation of Solid-Anchored DNA Oligomers" J.Am.Chem.Soc.112. 1691-1696 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H. Takaya, T. Ohta, N. Sayo, H. Kumobayashi, S. Akutagawa, S. Inoue, I. Kasahara, and R. Noyori: "Enantioselective Hydrogenation of Allylic and Homoallylic Alcohols." J. Am. Chem. Soc.109. 1596-1597 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R. Norori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, and S. Akutagawa: "Asymmetric Hydrogenation of beta-Keto Carboxylic Ester. A Practical, Purely Chemical Access to b-Hydroxy Esters in High Enantiomeric Purity." J. Am. Chem. Soc.109. 5856-5858 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Hayakawa, S. Wakabayashi, T. Nobori, and R. Noyori: "A General Approach to Nucleoside 3'- and 5'-Monophosphates." Tetrahedron Lett.28. 2259-2262 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Ohta, H. Takaya, M. Kitamura, K. Nagai, and R. Noyori: "Asymmetric Hydrogenation of Unsaturated Carboxylic Acids Catalyzed by BINAP-Ruthenium (II) Complexes." J. Org. Chem.52. 3174-3176 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Maruoka, T. Itoh, T. Shirasaka, and H. Yamamoto: "Asymmetric Hetero-Diels-Alder Reaction Catalyzed by Chiral Organoaluminum Reagent." J. Am. Chem. Soc.110. 310-312 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Suzuki, Y. Morita, A. Yanagisawa, B. J. Baker, P. J. Scheuer, and R. Noyori: "Synthesis and Structural Revision of (7E)- and (7Z)-Punaglandin 4." J. Org. Chem.53. 286-295 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Kitamura, T. Ohkuma, S. Inoue, N. Sayo, H. Kumobayashi, S. Akutagawa, T. Ohta, H. Takaya, and R. Noyori: "Homogeneous Asymmetric Hydrogenation of Functionalized Ketones." J. Am. Chem. Soc.110. 629-631 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Maruoka, Y. Araki, and H. Yamamoto: "Methylaluminum Bis (2, 6-ditert-butyl-4-methylphenoxide) as a Protecting Group for Multifunctional Molecules. Synthetic Utility in Selective Carbonyl Reductions." J. Am. Chem. Soc.110. 2650-2652 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Maruoka, T. Itoh, M. Sakurai, K. Nonoshita, and H. Yamamoto: "Amphiphilic Reactions by means of Exceptionally Bulky Organoaluminum Reagents. Rational Approach for Obtaining Unusual Equatorial, anti-Cram and 1, 4-Selectivity in Carbonyl Alkylation." J. Am. Chem. Soc.110. 3588-3597 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Suzuki, A. Yanagisawa, and R. Noyori: "The Three-Component Coupling Synthesis of Prostaglandins." J. Am. Chem. Soc.110. 4718-4726 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Maruoka and H. Yamamoto: "Organoaluminums in Organic Synthesis" Tetrahedron. 44. 5001-5032 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R. Norori: "Chemical Multiplication of Chirality : Science and Applications." Chem. Soc. Rev.18. 187-208 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Kitamura, S. Okada, S. Suga, and R. Noyori: "Enantioselective Addition of Dialkylzincs to Aldehyde Promoted by Chiral Amino Alcohols. Mechanism and Nonlinear Effect." J. Am. Chem. Soc.111. 4028-4036 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Maruoka, T. Ooi and H. Yamamoto: "Organoaluminum-Promoted Rearrangement of Epoxy Silyl Ethers to beta-Siloxy Aldehydes." J. Am. Chem. Soc.111. 6431-6432 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R. Noyori, T. Ikeda, T. Ohkuma, M. Widhalm, M. Kitamura, H. Takaya, S. Akutagawa, N. Sayo, T. Saito, T. Taketomi, and H. Kumobayashi: "Stereoselective Hydrogenation via Dynamic Kinetic Resolution." J. Am. Chem. Soc.111. 9134-9135 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Hayakawa, S. Wakabayashi, H. Kato, and R. Noyori: "The Allylic Protection Method in Solid-Phase Oligonucleotide Synthesis. An Efficient Preparation of Solid-Anchored DNA Oligomers." J. Am. Chem. Soc.112. 1691-1696 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R. Noyori: "Chiral Metal Complexes as Discriminating Molecular Catalysts." Science. 248. 1194-1199 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R. Noyori and M. Suzuki: "An Organometallic Way to Prostaglandins : The Three-Component Coupling Synthesis." Chemtracts-Org. Chem.3. 173-197 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Inoue, H. Takaya, K. Tani, S. Otsuka, T. Sato, and R. Noyori: "Mechanism of the Asymmetric Isomerization of Allylamines to Enamines Catalyzed by 2, 2'-Bis (diphenylphosphino)-1, 1'-binaphthyl-Rhodium Complexes." J. Am. Chem. Soc.112. 4897-4905 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Maruoka, S. Nagahara, and H. Yamamoto: "Molecular Recognition of Ethers with Modified Organoaluminum Reagents." J. Am. Chem. Soc.112. 6115-6117 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R. Noyori and H. Takaya: "BINAP : An Efficient Chiral Element for Asymmetric Catalysis." Acc. Chem. Res.23. 345-350 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Takaya, T. Ohta, K. Mashima, and R. Noyori: "New Chiral Ruthenium Complexes for Asymmetric Catalytic Hydrogenations." Pure Appl. Chem.62. 1135-1138 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Yamamoto and K. Maruoka: "Stereo- and Regioselective Organic Transformations Based on Main Group Organometallic Reagents-Application to the Stereocontrolled Claisen Rearrangements." Pure Appl. Chem.62. 2063-2068 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R. Noyori and M. Kitamura: "Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds : Chirality Transfer, Multiplication, and Amplification." Angew. Chem., Int. Ed. Engl.30. 49-69 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Suzuki, H. Koyano, R. Noyori, H. Hashimoto, M. Negishi, A. Ichikawa, and S. Ito: "An Azido-Functionalized Isocarbacyclin Analogue Acting as an Efficient Photoaffinity Probe for a Prostacyclin Receptor." Tetrahedron.

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1993-03-16  

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