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Cationic Palladium Complex-Catalyzed Hetero Diels-Alder Reaction

Research Project

Project/Area Number 08651015
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionTohoku University

Principal Investigator

OI Shuichi  Tohoku University, Graduate School of Engineering, Department of Materials Chemistry, Lecturer, 大学院・工学研究科, 講師 (00241547)

Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1997: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1996: ¥1,600,000 (Direct Cost: ¥1,600,000)
Keywordspalladium complex / hetero Diels-Alder reaction / asymmetric reaction / dihydropyran
Research Abstract

The hetero Diels-Alder reaction using carbonyl compounds as dienophiles has been a very useful method to construct the dihydropyran skeleton. However, it is necessary to use activated dienes containing strong electron-donating groups and/or activated carbonyl compounds containing electronwithdrawing groups to conduct the reaction smoothly under mild conditions. In this research project, we found that the hetero Diels-Alder reaction of nonactivated simple dienes with aldehydes is catalyzed by cationic palladium (II) complexes. Thus, the reaction of 2-methyl and 2,3-dimethyl substituted 1,3-butadienes with aromatic and aliphatic aldehydes proceeded smoothly at 50゚C for 20 h in the presence of 2 mol% of the cationic palladium (II) complexes, such as [Pd (dppp) (PhCN) _2] (BF_4) _2. In this reaction, we assume that the palladium complex acts as a Lewis acid catalyst. In the research of 1997, we investigated asymmetric hetero Diels-Alder reaction using chiral palladium complex. The reaction of phenylglyoxal with 2,3-dimethyl-1,3-butadiene, 1,3-cyclohexadiene, and 1,2-dimethylenecyclopentane in the presence of [Pd (S-BINAP) (PhCN) _2] (BF_4) _2 afforded the cyclization products in 95 to 99 %ee, respectively. It can be assumed that chelate coordination of the two carbonyl group of phenylglyoxal to palladium give rise to the high enantioselectivity.

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (4 results)

All Other

All Publications (4 results)

  • [Publications] Shuichi, Oi: "Cationic Palladium(II)Complex-Catalyzed Hetero Diels-Alder Reaction of Dienes with Aldehydes" Tetrahedron Letters. 37. 6351-6354 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shuichi Oi, Kenji Kashiwagi, Eiji Terada, Kazuei Ohuchi, and Yoshio Inoue: ""Cationic Palladium (II) Complex-Catalyzed Hetero Diels-Alder Reaction of Dienes with Aldehydes"" Tetrahedron Letters. Vol.37. 6351-6354 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shuichi Oi: "Cationic Palladium(II) Complex-Catalyzed Hetero Diels-Alder Reaction of Dienes with Aldehydes" Tetrahedron Letters. Vol.37,No.35. 6351-6354 (1996)

    • Related Report
      1997 Annual Research Report
  • [Publications] Shuichi Oi: "Cationic palladium (II) Complex-Catalyzed Hetero Diels-Alder Reaction of Dienes with Aldehydes" Tetrahedron Letters. Vol. 37 No. 35. 6351-6354 (1996)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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