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GENERATION OF αTRIFLUOROMETHYLATED ENOLATE SPECIES AND THEIR APPLICATION TO ASYMMETRIC ALDOL SYNTHESIS

Research Project

Project/Area Number 14550808
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionKyoto Institute of Technology

Principal Investigator

ISHIHARA Takashi  KYOTO INSTITUTE OF TECHNOLOGY, DEPARTMENT OF CHEMISTRY AND MATERIALS TECHNOLOGY, PROFESSOR, 工芸学部, 教授 (40093182)

Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 2003: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2002: ¥2,300,000 (Direct Cost: ¥2,300,000)
Keywordsα-trifluoromethylated enolate species / fluorinated α-bromopropanoic acid derivatives / phosphine-lewis acid / asymmetric aldol-type reaction / reductive coupling reaction / erythro-selectivity / diastereoselectivity / 含フッ素α-ブロモプロパンアミド / 含フッ素2-オキサゾリジノンイミド / トリフルオロプロパン酸エステル / Reformatsky反応 / テトラフルオロプロパンアミド / ルイス酸触媒-トリフェニルホスフィン / 立体選択的アルドール反応 / α-トリフルオロメチル-β-ヒドロキシエステル / α-トリフルオロメチル-β-ヒドロキシアミド
Research Abstract

When N-methoxy-N-methyl-2-bromo-2, 3, 3, 3-tetrafluropropanamide was allowed to react with various aldehydes under the influence of triphenylphosphine and a catalytic amount of titanium (IV) isopropoxide in dichloromethane at room temperature, (trifluoromethyl)-β-hydroxy amides preferentially in good to excellent yields.
In addition, the reactions of benzyl 2-bromo-2, 3, 3, 3-tetrafluoropro-panoate with various types of chiral imines, such as (S)-sulfinimines and imines derived from (S)-valine methyl ester or (S)-phenylglycine methyl ester, in the presence of zinc in tetrahydrofuran at room temperature were revealed to afford the threo-and erythro-isomers of α-fluoro-α-(trifluoromethyl) -β-amino esters with high diasteremeric excesses in fair to good chemical yields.

Report

(3 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • Research Products

    (5 results)

All Other

All Publications (5 results)

  • [Publications] K.Sato, T.Sekiguchi, T.Ishihara, T.Konno, H.Yamanaka: "Highly Stereoselective Aldol-type Reaction of 2-Bromo-2,3,3,3-tetrafluoropropan-amide with Aldehydes Leading to erythro-α-Fluoro-α-(trifluoromethyl)-β-hydroxy Amides"Chemistry Letters. Vol.33, No.2. 154-155 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Sekiguchi, K.Sato, T.Ishihara, T.Konno, H.Yamanaka: "Zinc-mediated Coupling Reaction of 2-Bromo-2,3,3,3-tetrafluoropropanoate with Various Chiral Imines. Simple and Effective Access to Optically Active α-Fluoro-α-(trifluoromethyl)-β-amino Esters"Chemistry Letters. Vol.33, No.6. (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Sato, T.Sekiguchi, T.Ishihara, T.Konno, H.Yamanaka: "Highly Stereoselective Aldol-type Reaction of 2-Bromo-2, 3, 3, 3-tetrafluoropropanamide with Aldehydes Leading to erythro-α-Fluoro-α-(trifluoromethyl) -β-hydroxy Amides"Chemistry Letters. 33 (No.2). 154-155 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Sekiguchi, K.Sato, T.Ishihara, T.Konno, H.Yamanaka: "Zinc-mediated Coupling Reaction of 2-Bromo-2, 3, 3, 3-tetrafluoropropanoate Access to Optically Active α-Fluoro-α-(trifluoromethyl) -β-amino Esters"Chemistry Letters. 33 (No.6) (in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Sato, T.Sekiguchi, T.Ishihara, T.Konno, H.Yamanaka: "Highly stereoselective aldol-type reaction of 2-bromo-2,3,3,3-tetrafluoropropanamide with aldehydes leading to erythro-α-fluoro-α-(trifluoromethyl)-β-hydroxy amides"Chemistry Letters. Vol.33,No.2. 154-155 (2004)

    • Related Report
      2003 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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