FR2981071B1 - Synthese versatile et stereospecifique d'acides amines gamma,delta-insatures par la reaction de wittig - Google Patents

Synthese versatile et stereospecifique d'acides amines gamma,delta-insatures par la reaction de wittig

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Publication number
FR2981071B1
FR2981071B1 FR1159112A FR1159112A FR2981071B1 FR 2981071 B1 FR2981071 B1 FR 2981071B1 FR 1159112 A FR1159112 A FR 1159112A FR 1159112 A FR1159112 A FR 1159112A FR 2981071 B1 FR2981071 B1 FR 2981071B1
Authority
FR
France
Prior art keywords
wittig
versatile
delta
unsaturated
reaction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
FR1159112A
Other languages
English (en)
Other versions
FR2981071A1 (fr
Inventor
Sylvain Juge
Jerome Bayardon
Emmanuelle Remond
Marie-Joelle Ondel-Eymin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Centre National de la Recherche Scientifique CNRS
Universite de Bourgogne
Original Assignee
Centre National de la Recherche Scientifique CNRS
Universite de Bourgogne
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to FR1159112A priority Critical patent/FR2981071B1/fr
Application filed by Centre National de la Recherche Scientifique CNRS, Universite de Bourgogne filed Critical Centre National de la Recherche Scientifique CNRS
Priority to JP2014527630A priority patent/JP6021918B2/ja
Priority to EP12751338.0A priority patent/EP2751124B1/fr
Priority to CN201280052910.3A priority patent/CN103889994B/zh
Priority to US14/241,561 priority patent/US9242925B2/en
Priority to PCT/EP2012/066686 priority patent/WO2013030193A1/fr
Priority to CN201710459607.XA priority patent/CN107253968B/zh
Publication of FR2981071A1 publication Critical patent/FR2981071A1/fr
Application granted granted Critical
Publication of FR2981071B1 publication Critical patent/FR2981071B1/fr
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5456—Arylalkanephosphonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/02—Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00—Metallocenes
    • C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5435—Cycloaliphatic phosphonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C40—COMBINATORIAL TECHNOLOGY
    • C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
    • C40B40/00—Libraries per se, e.g. arrays, mixtures
    • C40B40/04—Libraries containing only organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
FR1159112A 2011-08-29 2011-10-10 Synthese versatile et stereospecifique d'acides amines gamma,delta-insatures par la reaction de wittig Expired - Fee Related FR2981071B1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
FR1159112A FR2981071B1 (fr) 2011-10-10 2011-10-10 Synthese versatile et stereospecifique d'acides amines gamma,delta-insatures par la reaction de wittig
EP12751338.0A EP2751124B1 (fr) 2011-08-29 2012-08-28 Synthèse polyvalente et stéréospécifique d'aminoacides gamma,delta-insaturés par la réaction de wittig
CN201280052910.3A CN103889994B (zh) 2011-08-29 2012-08-28 通过维悌希反应的进行γ，δ‑不饱和氨基酸的通用和立体有择合成
US14/241,561 US9242925B2 (en) 2011-08-29 2012-08-28 Versatile and stereospecific synthesis of γ,δ-unsaturated amino acids by Wittig reaction
JP2014527630A JP6021918B2 (ja) 2011-08-29 2012-08-28 ウィッティヒ反応によるγ，δ−不飽和アミノ酸の汎用的な立体特異的合成
PCT/EP2012/066686 WO2013030193A1 (fr) 2011-08-29 2012-08-28 Synthèse polyvalente et stéréospécifique d'aminoacides gamma,delta-insaturés par la réaction de wittig
CN201710459607.XA CN107253968B (zh) 2011-08-29 2012-08-28 通过维悌希反应的γ,δ-不饱和氨基酸的通用和立体有择合成

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1159112A FR2981071B1 (fr) 2011-10-10 2011-10-10 Synthese versatile et stereospecifique d'acides amines gamma,delta-insatures par la reaction de wittig

Publications (2)

Publication Number Publication Date
FR2981071A1 FR2981071A1 (fr) 2013-04-12
FR2981071B1 true FR2981071B1 (fr) 2014-02-07

Family

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FR1159112A Expired - Fee Related FR2981071B1 (fr) 2011-08-29 2011-10-10 Synthese versatile et stereospecifique d'acides amines gamma,delta-insatures par la reaction de wittig

Country Status (6)

Country Link
US (1) US9242925B2 (fr)
EP (1) EP2751124B1 (fr)
JP (1) JP6021918B2 (fr)
CN (2) CN103889994B (fr)
FR (1) FR2981071B1 (fr)
WO (1) WO2013030193A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3038605B1 (fr) 2015-07-06 2018-08-24 Universite Amiens Picardie Jules Verne Diamines primaires vicinales associees a des motifs chelateurs de metaux et/ou de radicaux libres, actives contre les stress carbonyle et oxydant et leur utilisation
CN106518816A (zh) * 2016-08-31 2017-03-22 浙江安赛生物科技股份有限公司 2‑苯基‑3‑(2‑呋喃基)丙‑2‑烯醛的制备工艺
CN110330446A (zh) * 2019-07-21 2019-10-15 滁州学院 一种含γ烯基或β烯基的非天然氨基酸的制备方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6133148A (ja) * 1984-07-25 1986-02-17 Suntory Ltd シクロプロピルアラニン誘導体の製造法
US5559256A (en) * 1992-07-20 1996-09-24 E. R. Squibb & Sons, Inc. Aminediol protease inhibitors
JP3583928B2 (ja) * 1997-08-15 2004-11-04 中外製薬株式会社 フェネチルアミン誘導体
GB9809664D0 (en) * 1998-05-06 1998-07-01 Hoffmann La Roche a-Ketoamide derivatives
FR2806722B1 (fr) * 2000-03-23 2002-05-17 Sanofi Synthelabo Derives de n-(heterocyclylbutyl) benzene-ou pyridine sulfonamide, leur preparation et leur application en therapeutique
CN102584940B (zh) * 2005-01-13 2014-12-31 卧龙岗大学 肽化合物
CN101472900B (zh) * 2006-06-19 2011-07-27 东丽株式会社 多发性硬化症的治疗或预防药
US7659270B2 (en) * 2006-08-11 2010-02-09 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
JP4117009B2 (ja) * 2006-11-14 2008-07-09 サントリー株式会社 ムギネ酸類の効率的製造方法
US7772221B2 (en) * 2007-02-09 2010-08-10 Bristol-Meyers Squibb Company Diaminopropane derived macrocycles as inhibitors of β amyloid production
CN101284797B (zh) * 2008-06-11 2010-08-11 常州恩滋生物科技有限公司 N-保护的烯丙基甘氨酸酯的拆分方法
US8580998B2 (en) * 2008-12-11 2013-11-12 University Of Georgia Research Foundation, Inc. Preparation of alkenes by mild thermolysis of sulfoxides

Also Published As

Publication number Publication date
EP2751124A1 (fr) 2014-07-09
CN107253968A (zh) 2017-10-17
FR2981071A1 (fr) 2013-04-12
CN103889994A (zh) 2014-06-25
US9242925B2 (en) 2016-01-26
CN103889994B (zh) 2017-07-11
JP2014527539A (ja) 2014-10-16
EP2751124B1 (fr) 2018-05-16
JP6021918B2 (ja) 2016-11-09
CN107253968B (zh) 2020-03-13
WO2013030193A1 (fr) 2013-03-07
US20140364339A1 (en) 2014-12-11

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