HUP0103428A2 - Új eljárás optikailag aktív alfa-amino-nitrilek előállítására - Google Patents

Új eljárás optikailag aktív alfa-amino-nitrilek előállítására

Info

Publication number
HUP0103428A2
HUP0103428A2 HU0103428A HUP0103428A HUP0103428A2 HU P0103428 A2 HUP0103428 A2 HU P0103428A2 HU 0103428 A HU0103428 A HU 0103428A HU P0103428 A HUP0103428 A HU P0103428A HU P0103428 A2 HUP0103428 A2 HU P0103428A2
Authority
HU
Hungary
Prior art keywords
aminonitriles
optically active
novel method
general formula
preparing optically
Prior art date
Application number
HU0103428A
Other languages
English (en)
Inventor
Janice Byrne
Pierre-Yves Chavant
Murielle Chavarot
Vivien Henryon
Yannick Vallee
Original Assignee
Aventis Cropscience S.A.
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 Aventis Cropscience S.A. filed Critical Aventis Cropscience S.A.
Publication of HUP0103428A2 publication Critical patent/HUP0103428A2/hu

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/226—Sulfur, e.g. thiocarbamates
    • 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
    • C07C227/30—Preparation of optical isomers
    • C07C227/32—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/20—Free hydroxyl or mercaptan
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/322—Hydrocyanation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0213—Complexes without C-metal linkages
    • B01J2531/0216—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/31—Aluminium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/32—Gallium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/35—Scandium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/38—Lanthanides other than lanthanum
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/46—Titanium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/48—Zirconium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/49—Hafnium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

A találmány új eljárásra vonatkozik (I) általános képletű optikailagaktív a-aminonitrilek előállítására. Az eljárás során (II) általánosképletű ketimineket hidrociánoznak hidrociánozó reagens segítségévelkatalizátorként ható királis vagy kiralitás induktor fém-komplexjelenlétében. A képletekben R1, R2 és T jelentése a leírás szerinti.Az (I) általános képletű a-aminonitrileket optikailag aktív szervesvegyületek szintéziséhez intermedierként lehet felhasználni. Ó
HU0103428A 1999-06-09 2000-06-09 Új eljárás optikailag aktív alfa-amino-nitrilek előállítására HUP0103428A2 (hu)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9907512A FR2794743A1 (fr) 1999-06-09 1999-06-09 Nouveau procede de preparation d'alpha-aminonitriles optiquement actifs
PCT/FR2000/001597 WO2000075104A1 (fr) 1999-06-09 2000-06-09 NOUVEAU PROCEDE DE PREPARATION D'α-AMINONITRILES OPTIQUEMENT ACTIFS

Publications (1)

Publication Number Publication Date
HUP0103428A2 true HUP0103428A2 (hu) 2002-01-28

Family

ID=9546766

Family Applications (1)

Application Number Title Priority Date Filing Date
HU0103428A HUP0103428A2 (hu) 1999-06-09 2000-06-09 Új eljárás optikailag aktív alfa-amino-nitrilek előállítására

Country Status (11)

Country Link
EP (1) EP1102744A1 (hu)
JP (1) JP2003501411A (hu)
KR (1) KR20010072385A (hu)
CN (1) CN1314880A (hu)
AU (1) AU5540900A (hu)
BR (1) BR0006829A (hu)
FR (1) FR2794743A1 (hu)
HU (1) HUP0103428A2 (hu)
PL (1) PL345995A1 (hu)
TR (1) TR200100435T1 (hu)
WO (1) WO2000075104A1 (hu)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2398569B (en) * 2003-02-19 2006-12-27 Merck Patent Gmbh Chiral compounds comprising Group IV element with two 1,1'-binaphth-2,2'-diyl-containing or related substituents
US20100179343A1 (en) * 2007-03-29 2010-07-15 Agency For Science, Technology And Research Method of producing an optically active cyanohydrin derivative
JP5426556B2 (ja) * 2007-09-28 2014-02-26 エージェンシー フォー サイエンス，テクノロジー アンド リサーチ イミンの不斉シアノ化方法
WO2010071227A1 (en) * 2008-12-17 2010-06-24 Takasago International Corporation Aluminium complexes and use thereof as a catalyst in intramolecular ring closure reactions
JP5501701B2 (ja) * 2009-09-09 2014-05-28 三井化学株式会社 イミンの不斉シアノ化方法
CN103342652B (zh) * 2013-07-24 2015-02-25 重庆紫光化工股份有限公司 N,n-二甲基氨基乙酸酯的制备方法
CN103962180B (zh) * 2013-08-06 2016-02-17 汕头大学 用于制备α-氨基腈的Salen配位聚合物催化剂及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2706456B1 (fr) * 1993-06-18 1996-06-28 Rhone Poulenc Agrochimie Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides.
FR2751327A1 (fr) * 1996-07-22 1998-01-23 Rhone Poulenc Agrochimie Intermediaires pour la preparation de 2-imidazoline-5-ones

Also Published As

Publication number Publication date
BR0006829A (pt) 2001-10-30
FR2794743A1 (fr) 2000-12-15
WO2000075104A1 (fr) 2000-12-14
PL345995A1 (en) 2002-01-14
EP1102744A1 (fr) 2001-05-30
CN1314880A (zh) 2001-09-26
TR200100435T1 (tr) 2001-08-21
KR20010072385A (ko) 2001-07-31
JP2003501411A (ja) 2003-01-14
AU5540900A (en) 2000-12-28

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