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Stereoselective construction of quaterary stereogenic center

Research Project

Project/Area Number 25410113
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionToyohashi University of Technology

Principal Investigator

SHIBATOMI Kazutaka  豊橋技術科学大学, 工学(系)研究科(研究院), 准教授 (00378259)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords不斉合成 / ハロゲン化合物 / SN2反応 / 二型糖尿病治療薬 / 第三級アルコール / フェノキシド / 不斉触媒 / キラルルイス酸 / 触媒的不斉合成 / 不斉塩素化反応 / アリールエーテル / 三級アルコール / 糖尿病治療薬 / フェノキシ化反応 / Williamson合成 / 塩素化反応
Outline of Final Research Achievements

Asymmetric synthesis of chiral organic molecules is a highly useful synthetic method for the preparation of various functional molecules. In particular, development of flexible methods for the preparation of compounds with a chiral quaternary stereogenic center is strongly required in medicinal chemistry. Previously, we succeeded in the enantioselective chlorination of b-keto esters with newly developed chiral Lewis acid catalyst. Here, we found that the SN2 reactions of resulting chlorides afforded the corresponding substituted products without loss of enantiopurity with water or phenol as the nucleophile. Furthermore, we demonstrated that the resulting substituted products could be converted into potential candidates of anti-diabetic drug.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (33 results)

All 2016 2015 2014 2013 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Open Access: 1 results,  Acknowledgement Compliant: 2 results) Presentation (27 results) (of which Int'l Joint Research: 9 results,  Invited: 7 results) Remarks (1 results)

  • [Journal Article] Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C-F bond cleavage2016

    • Author(s)
      Shibatomi, K.; Kitahara, K.; Okimi, T.; Abe, Y.; Iwasa, S.
    • Journal Title

      Chemical Science

      Volume: 7 Issue: 2 Pages: 1388-1392

    • DOI

      10.1039/c5sc03486h

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Williamson Ether Synthesis with Phenols at a Tertiary Stereogenic Carbon: Formal Enantioselective Phenoxylation of β-Keto Esters2015

    • Author(s)
      Shibatomi, K.; Kotozaki, M.; Sasaki, N.; Fujisawa, I.; Iwasa, S.
    • Journal Title

      Chemistry A European Journal

      Volume: 21 Issue: 40 Pages: 14095-14098

    • DOI

      10.1002/chem.201502042

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Catalytic Enantioselective Constructions of Trifluoromethylated Chiral Stereogenic Centers via the Conjugate Addition to CF3-Alkenes: Overview of Current Progress2015

    • Author(s)
      Shibatomi, K.
    • Journal Title

      Current Organic Chemistry

      Volume: 19 Pages: 1619-1637

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution2014

    • Author(s)
      K. Shibatomi, T. Okimi, Y. Abe, A. Narayama, N. Nakamura, S. Iwasa
    • Journal Title

      Beilstein Journal of Organic Chemistry

      Volume: 10 Pages: 323-331

    • DOI

      10.3762/bjoc.10.30

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] ルイス酸触媒および有機分子触媒を活用した含ハロゲン化合物の高エナンチオ選択的合成法の開発2014

    • Author(s)
      柴富一孝
    • Journal Title

      有機合成化学協会誌

      Volume: 72 Pages: 232-245

    • NAID

      130003395390

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Organocatalytic Decarboxylative Halogenation of β-Keto Carboxylic Acids2016

    • Author(s)
      SHIBATOMI, Kazutaka; KAWASAKI, Yohei; SASAKI, Nozomi; IWASA, Seiji
    • Organizer
      日本化学会第96春期年会
    • Place of Presentation
      京都
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 有機分子触媒を用いたα―ハロ―β―ケトエステルの脱炭酸型不斉プロトン化反応2016

    • Author(s)
      佐々木希、柴富一孝、岩佐精二
    • Organizer
      日本化学会第96春期年会
    • Place of Presentation
      京都
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Asymmetric Synthesis of Halogenated Compounds Directed Toward Drug Development2016

    • Author(s)
      Shibatomi, K.
    • Organizer
      The 3rd International Conference of Global Network for Innovative Technology (IGNITE 2016)
    • Place of Presentation
      Penang (Malaysia)
    • Year and Date
      2016-01-27
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Williamson ether synthesis at a tertiary stereogenic carbon: a new synthetic route to anti-diabetic drugs2016

    • Author(s)
      Sasaki, N.; Kotozaki, M.; Shibatomi, K.; Iwasa, S.
    • Organizer
      The 3rd International Conference of Global Network for Innovative Technology (IGNITE 2016)
    • Place of Presentation
      Penang (Malaysia)
    • Year and Date
      2016-01-27
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Highly enantioselective fluorination of branched aldehydes and its application for the synthesis of fluorinated biologically active molecules2016

    • Author(s)
      Kitaharam K.; Okimi, T.; Abe, Y.; Shibatomi, K.; Iwasa, S.
    • Organizer
      The 3rd International Conference of Global Network for Innovative Technology (IGNITE 2016)
    • Place of Presentation
      Penang (Malaysia)
    • Year and Date
      2016-01-27
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Hunsdiecker型反応によるα―ハロケトンの触媒的不斉反応2016

    • Author(s)
      佐々木希、川崎洋平、柴富一孝、岩佐精ニ
    • Organizer
      「有機分子触媒による未来型分子変換」第6回公開シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2016-01-22
    • Related Report
      2015 Annual Research Report
  • [Presentation] Asymmetric Favorskii Rearrangement of α-Chloro-β-keto Esters2015

    • Author(s)
      Sasaki, N.; Kotozaki, M.; Shibatomi, K.; Iwasa, S.
    • Organizer
      The International Chemical Congress of Pacific Basin Society 2015 (Pacifichem 2015)
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Highly enantioselective fluorination of α-branched aldehydes with a newly developed chiral primary amine catalyst2015

    • Author(s)
      Kitahara, K.; Okimi, T.; Shibatomi, K.; Iwasa, S.
    • Organizer
      The International Chemical Congress of Pacific Basin Society 2015 (Pacifichem 2015)
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Organocatalytic enantioselective fluorination of α,α-disubstituted aldehydes2015

    • Author(s)
      Shibatomi, K.; Kitahara, K.; Okimi, T.; Narayama, A.; Iwasa, S.
    • Organizer
      The International Chemical Congress of Pacific Basin Society 2015 (Pacifichem 2015)
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 新規キラルー級アミン触媒の開発と分岐型アルデヒドの不斉ハロゲン化反応への応用2015

    • Author(s)
      北原一利,沖見卓哉,柴富一孝, 岩佐精二
    • Organizer
      第46回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      三重
    • Year and Date
      2015-11-07
    • Related Report
      2015 Annual Research Report
  • [Presentation] Development of New Chiral Primary Amine Catalyst and Its Application to the Enantioselective Halogenation of α-Branched Aldehydes2015

    • Author(s)
      Shibatomi, K.; Kitahara, K.; Okimi, T.; Abe, Y.; Iwasa, S.
    • Organizer
      21st International Symposium on Fluorine Chemistry
    • Place of Presentation
      Como (Italy)
    • Year and Date
      2015-08-23
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Asymmetric synthesis of α-heteroatom-substituted β-keto esters via SN2 substitution of tertiary chlorides2015

    • Author(s)
      Shibatomi, K.; Kotozaki, M.; Sasaki, N.; Iwasa, S
    • Organizer
      250th ACS National Meeting
    • Place of Presentation
      Boston (USA)
    • Year and Date
      2015-08-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of New Chiral Primary Amine Catalyst and Its Use for Enantioselective Fluorination of α-Branched Aldehydes2015

    • Author(s)
      K. Shibatomi
    • Organizer
      The 39th Naito Conference
    • Place of Presentation
      Sapporo (Japan)
    • Year and Date
      2015-07-06
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] フェノール類を用いた三級不斉炭素上でのWilliamsonエーテル合成2015

    • Author(s)
      琴崎 真任・佐々木 希・柴富 一孝・岩佐 精二
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部 船橋キャンパス、千葉
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] α-クロロ-β-ケトエステルのFavorskii転移反応2014

    • Author(s)
      佐々木希, 琴崎真任, 柴富一孝, 岩佐精二
    • Organizer
      第45回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      中部大学春日井キャンパス、愛知
    • Year and Date
      2014-11-29 – 2014-11-30
    • Related Report
      2014 Research-status Report
  • [Presentation] Enantioselective synthesis of chiral fluorinated molecules2014

    • Author(s)
      K. Shibatomi
    • Organizer
      The 5th China-Japan-Korea Joint Seminar on Fluorine Chemistry
    • Place of Presentation
      Shanghai, China
    • Year and Date
      2014-10-19 – 2014-10-21
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] キラル三級塩素化物のSN2反応によるα-フェノキシ-β-ケトエステルの不斉合成2014

    • Author(s)
      琴崎真任, 佐々木希, 柴富一孝, 岩佐精二
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      タワーホール船堀、東京
    • Year and Date
      2014-10-14 – 2014-10-16
    • Related Report
      2014 Research-status Report
  • [Presentation] Enantioselective Bromination of Active Methine Compounds Using Chiral Lewis Acid Catalyst2014

    • Author(s)
      延命千浩, 柴富一孝, 岩佐精二
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学、福岡
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Research-status Report
  • [Presentation] スピロ型キラルオキサゾリン配位子を用いた活性メチン化合物の不斉ハロゲン化反応2014

    • Author(s)
      延命千浩, 楢山輝, 柴富一孝, 岩佐精二
    • Organizer
      第4回フッ素化学若手の会
    • Place of Presentation
      舘山寺温泉開華亭、浜松
    • Year and Date
      2014-08-08 – 2014-08-09
    • Related Report
      2014 Research-status Report
  • [Presentation] Copper(II)-Catalyzed Enantioselective Chlorination of β-Keto Esters and Subsequent SN2 Displacement of Chiral Tertiary Chlorides Using Oxygen Nucleophiles2014

    • Author(s)
      M. Kotozaki, A. Narayama, K. Shibatomi, S. Iwasa
    • Organizer
      XXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      Royton Sapporo、札幌
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Research-status Report
  • [Presentation] Lewis Acid-Catalyzed Asymmetric Chlorination of Active Methine Compounds and Susequent SN2 Substitution2014

    • Author(s)
      K. Shibatomi, M. Kotozaki, Y. Soga, A. Narayama, S. Iwasa
    • Organizer
      Zing Conference-Asymmetric Synthesis-
    • Place of Presentation
      Malaga, Spain
    • Related Report
      2013 Research-status Report
  • [Presentation] Enantioselective Construction of Fluorinated Chiral Carbon Centers2013

    • Author(s)
      K. Shibatomi
    • Organizer
      17th European Symposium on Fluorine Chemistry
    • Place of Presentation
      Paris, France
    • Related Report
      2013 Research-status Report
  • [Presentation] 有機ハロゲン化合物の触媒的不斉合成2013

    • Author(s)
      柴富一孝
    • Organizer
      平成25年度第7回グリーン元素講演会
    • Place of Presentation
      岡山理科大学
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] キラルルイス酸触媒を用いた活性メチン化合物の不斉臭素化反応2013

    • Author(s)
      延命千浩, 柴富一孝, 岩佐精二
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      静岡大学
    • Related Report
      2013 Research-status Report
  • [Presentation] フッ素原子を有する不斉炭素のエナンチオ選択的な構築手法2013

    • Author(s)
      柴富一孝
    • Organizer
      第7回フッ素化学セミナー
    • Place of Presentation
      つくば国際会議場
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] ルイス酸触媒および有機分子触媒を活用した含ハロゲン化合物の高エナンチオ選択的合成法の開発2013

    • Author(s)
      柴富一孝
    • Organizer
      第30回有機合成化学セミナー
    • Place of Presentation
      せとうち児島ホテル
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] ハロゲン化された不斉炭素のエナンチオ選択的構築法2013

    • Author(s)
      柴富一孝
    • Organizer
      平成25年度有機合成セミナー
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
    • Invited
  • [Remarks] 豊橋技術科学大学 有機反応化学研究室HP

    • URL

      http://ens.tut.ac.jp/orgchem/index.html

    • Related Report
      2015 Annual Research Report

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Published: 2014-07-25   Modified: 2019-07-29  

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