WO2004026806A3 - Procede de preparation diastereoselectif d'olefines par la reaction d'horner-wadsworth-emmons comprenant un ajout d'un agent sequestrant tris-(polyoxaalkyl)-amine - Google Patents

Procede de preparation diastereoselectif d'olefines par la reaction d'horner-wadsworth-emmons comprenant un ajout d'un agent sequestrant tris-(polyoxaalkyl)-amine Download PDF

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Publication number
WO2004026806A3
WO2004026806A3 PCT/FR2003/002781 FR0302781W WO2004026806A3 WO 2004026806 A3 WO2004026806 A3 WO 2004026806A3 FR 0302781 W FR0302781 W FR 0302781W WO 2004026806 A3 WO2004026806 A3 WO 2004026806A3
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WO
WIPO (PCT)
Prior art keywords
polyoxaalkyl
wadsworth
horner
tris
addition
Prior art date
Application number
PCT/FR2003/002781
Other languages
English (en)
Other versions
WO2004026806A2 (fr
Inventor
Francois Touchard
Olivier Buisine
Guyader Frederic Le
Thierry Schlama
Franco Manfre
Original Assignee
Rhodia Cons Spec Ltd
Francois Touchard
Olivier Buisine
Guyader Frederic Le
Thierry Schlama
Franco Manfre
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
Application filed by Rhodia Cons Spec Ltd, Francois Touchard, Olivier Buisine, Guyader Frederic Le, Thierry Schlama, Franco Manfre filed Critical Rhodia Cons Spec Ltd
Priority to US10/528,715 priority Critical patent/US20060100456A1/en
Priority to CA002499635A priority patent/CA2499635A1/fr
Priority to AU2003279429A priority patent/AU2003279429A1/en
Priority to EP03772375A priority patent/EP1549607A2/fr
Publication of WO2004026806A2 publication Critical patent/WO2004026806A2/fr
Publication of WO2004026806A3 publication Critical patent/WO2004026806A3/fr

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Classifications

    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/48—Aldehydo radicals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)

Abstract

L'invention concerne un procédé de préparation diastéréosélectif d'oléfines par la réaction d'Horner-Wadsworth-Emmons consistant à faire réagir à basse température un phosphonate sur un dérivé carbonylé en présence d'une base dans un solvant approprié, caractérisé en ce qu'on ajoute dans une quantité suffisante pour augmenter la diastéréosélectivité de l'oléfine un agent séquestrant tris-(polyoxaalkyl)-amine de formule (I) :N-[CHR1-CHR2-O-(CHR3-CHR4-O)n-R5]3 (I). Dans laquelle : n est un nombre entier compris entre 0 et 10 ;R1, R2, R3, R4 peuvent être identiques ou différents, et représentent un atome d'hydrogène ou un radical alkyle ayant de 1 à 4 atomes de carbone ;R5 représente un atome d'hydrogène, un radical alkyle ou cycloalkyle ayant jusqu'à 12 atomes de carbone , un radical phényle ou un radical de formule -CmH2m-Φ- , ou CmH2m+1-Φ , avec m étant un nombre entier compris entre 1 et 12 et Φ étant un radical phényle.
PCT/FR2003/002781 2002-09-23 2003-09-22 Procede de preparation diastereoselectif d'olefines par la reaction d'horner-wadsworth-emmons comprenant un ajout d'un agent sequestrant tris-(polyoxaalkyl)-amine WO2004026806A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US10/528,715 US20060100456A1 (en) 2002-09-23 2003-09-22 Diastereoselective method of preparing olefins by means of the horner-wadsworthemmons reaction, comprising the addition of a tris-(polyoxaalkyl)-amine sequestering agent
CA002499635A CA2499635A1 (fr) 2002-09-23 2003-09-22 Procede de preparation diastereoselectif d'olefines par la reaction d'horner-wadsworth-emmons comprenant un ajout d'un agent sequestrant tris-(polyoxaalkyl)-amine
AU2003279429A AU2003279429A1 (en) 2002-09-23 2003-09-22 Diastereoselective method of preparing olefins by means of the horner-wadsworth-emmons reaction, comprising the addition of a tris-(polyoxaalkyl)-amine sequestering agent
EP03772375A EP1549607A2 (fr) 2002-09-23 2003-09-22 Procede de preparation diastereoselectif d'olefines par la reaction d'horner-wadsworth-emmons comprenant un ajout d'un agent sequestrant tris-(polyoxaalkyl)-amine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR02/11731 2002-09-23
FR0211731A FR2844791B1 (fr) 2002-09-23 2002-09-23 Procede de preparation diastereoselectif d'olefines par la reaction d'horner-wadsworth-emmons comprenant un ajout d'un agent sequestrant tris-(polyoxaalkyl)-amine

Publications (2)

Publication Number Publication Date
WO2004026806A2 WO2004026806A2 (fr) 2004-04-01
WO2004026806A3 true WO2004026806A3 (fr) 2004-04-22

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2003/002781 WO2004026806A2 (fr) 2002-09-23 2003-09-22 Procede de preparation diastereoselectif d'olefines par la reaction d'horner-wadsworth-emmons comprenant un ajout d'un agent sequestrant tris-(polyoxaalkyl)-amine

Country Status (7)

Country Link
US (1) US20060100456A1 (fr)
EP (1) EP1549607A2 (fr)
CN (1) CN100378059C (fr)
AU (1) AU2003279429A1 (fr)
CA (1) CA2499635A1 (fr)
FR (1) FR2844791B1 (fr)
WO (1) WO2004026806A2 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL2519100T3 (pl) 2009-12-29 2017-09-29 Mapi Pharma Limited Związki pośrednie i sposoby wytwarzania tapentadolu i pokrewnych związków
CN103102256A (zh) * 2013-01-24 2013-05-15 复旦大学 一种光学活性7-取代氧基-6-羟基庚-3-乙烯-2-酮的制备方法
CN103145540B (zh) * 2013-03-17 2015-07-29 复旦大学 一种光学活性7-卤代-6-羟基-庚-3-烯-2-酮的制备方法
CN105152973B (zh) * 2015-08-20 2017-04-12 浙江工业大学 一种二苯乙烯衍生物及其制备方法和应用
CN106674255B (zh) * 2016-12-21 2018-11-13 南京工业大学 致电变色化合物单体bedot-v-p及合成和应用
CN109438357A (zh) * 2018-11-05 2019-03-08 重庆科脉生物化工有限公司 一种咪唑类医药中间体kk-42的制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10203122A1 (de) * 2002-01-25 2003-07-31 Gruenenthal Gmbh Verfahren zur Herstellung von substituierten Acrylsäureestern bzw. deren Einsatz zur Herstellung von substituierten gamma-Aminosäuren

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
GÉRARD SOULA: "Tris(polyoxaalkyl)amines (Trident), anew class of solid-liquid phase-transfer catalysts", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 50, no. 20, 4 October 1985 (1985-10-04), pages 3717 - 3721, XP002105964, ISSN: 0022-3263 *
J. E. MCMURRY ET AL.: "An Efficient Method for the preparation of Alkylidenecyclopropanes", TETRAHEDRON LETTERS., vol. 29, no. 21, 1988, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 2531 - 2534, XP002244910, ISSN: 0040-4039 *
J. MOTOYOSHIYA: "Recent development of Z-selective Horner-Wadsworth-Emmons reaction", TRENDS IN ORGANIC CHEMISTRY, vol. 7, 1998, XX, XX, pages 63 - 73, XP008017925 *
N. DAUBRESSE: "Phase Transfer Wittig Reaction with 1,3-Dioxolan-2-yl-methyltriphenyl phosphonium Salts", TETRAHEDRON., vol. 54, 1998, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 10761 - 10770, XP002244911, ISSN: 0040-4020 *
W. C. STILL, C. GENNARI: "Direct Synthesis of Z-Unsaturated Esters", TETRAHEDRON LETTERS., vol. 24, no. 41, 1983, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 4405 - 4408, XP001149087, ISSN: 0040-4039 *

Also Published As

Publication number Publication date
US20060100456A1 (en) 2006-05-11
AU2003279429A8 (en) 2004-04-08
WO2004026806A2 (fr) 2004-04-01
CN100378059C (zh) 2008-04-02
FR2844791A1 (fr) 2004-03-26
FR2844791B1 (fr) 2004-10-29
EP1549607A2 (fr) 2005-07-06
CN1684939A (zh) 2005-10-19
CA2499635A1 (fr) 2004-04-01
AU2003279429A1 (en) 2004-04-08

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