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WO2012153991A3 - Procédé de préparation d'un α-aminonitrile chiral à l'aide d'un catalyseur pour une réaction de strecker - Google Patents

Procédé de préparation d'un α-aminonitrile chiral à l'aide d'un catalyseur pour une réaction de strecker Download PDF

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Publication number
WO2012153991A3
WO2012153991A3 PCT/KR2012/003666 KR2012003666W WO2012153991A3 WO 2012153991 A3 WO2012153991 A3 WO 2012153991A3 KR 2012003666 W KR2012003666 W KR 2012003666W WO 2012153991 A3 WO2012153991 A3 WO 2012153991A3
Authority
WO
WIPO (PCT)
Prior art keywords
aminonitrile
alkali metal
present
catalyst
cyanide
Prior art date
Application number
PCT/KR2012/003666
Other languages
English (en)
Korean (ko)
Other versions
WO2012153991A2 (fr
Inventor
송충의
오중석
양하롱
Original Assignee
성균관대학교 산학협력단
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 성균관대학교 산학협력단 filed Critical 성균관대학교 산학협력단
Publication of WO2012153991A2 publication Critical patent/WO2012153991A2/fr
Publication of WO2012153991A3 publication Critical patent/WO2012153991A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/32—Separation; Purification; Stabilisation; Use of additives
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • 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
    • B01J31/2213—At least two complexing oxygen atoms present in an at least bidentate or bridging ligand
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • 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
    • C07C255/25—Aminoacetonitriles
    • 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • 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
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • 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
    • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne un procédé de préparation d'un α-aminonitrile chiral par une réaction de Strecker par utilisation d'une source de cyanure sous un catalyseur ayant la Formule Chimique 1 ou la Formule Chimique 2 de dérivés d'éthylène glycol. Selon la présente invention, des α-aminonitriles chiraux ayant diverses structures et une stéréosélectivité élevée peuvent être synthétisés. De plus, un α-aminonitrile de type (R), qui est un précurseur d'un acide aminé pouvant être obtenu de manière synthétique, un acide (R)-α-aminé, peut être synthétisé pour avoir une pureté optique élevée. Comme source de cyanure, un cyanure de métal alcalin ayant une bonne stabilité thermique, de bonnes propriétés de stockage, un faible coût et des propriétés de facilité d'utilisation, peut être utilisé seulement, ou une combinaison du cyanure de métal alcalin et d'un sulfinate de métal alcalin ou d'acide sulfinique peut être utilisée. Le procédé selon la présente invention est très utile en développement industriel, très économique et simple.
PCT/KR2012/003666 2011-05-12 2012-05-10 Procédé de préparation d'un α-aminonitrile chiral à l'aide d'un catalyseur pour une réaction de strecker WO2012153991A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20110044666 2011-05-12
KR10-2011-0044666 2011-05-12

Publications (2)

Publication Number Publication Date
WO2012153991A2 WO2012153991A2 (fr) 2012-11-15
WO2012153991A3 true WO2012153991A3 (fr) 2013-03-21

Family

ID=47139820

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2012/003666 WO2012153991A2 (fr) 2011-05-12 2012-05-10 Procédé de préparation d'un α-aminonitrile chiral à l'aide d'un catalyseur pour une réaction de strecker

Country Status (2)

Country Link
KR (1) KR101430116B1 (fr)
WO (1) WO2012153991A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG11201607443XA (en) 2014-03-13 2016-10-28 Mitsubishi Gas Chemical Co Resist composition and method for forming resist pattern
TWI659013B (zh) 2014-03-13 2019-05-11 日商三菱瓦斯化學股份有限公司 化合物、樹脂、微影蝕刻用底層膜形成材料、微影蝕刻用底層膜、圖型形成方法、及化合物或樹脂的純化方法
JP6156711B2 (ja) * 2015-03-30 2017-07-05 三菱瓦斯化学株式会社 レジスト基材、レジスト組成物及びレジストパターン形成方法
JP6939544B2 (ja) 2015-03-30 2021-09-22 三菱瓦斯化学株式会社 化合物、樹脂、及びそれらの精製方法、リソグラフィー用の下層膜形成材料、下層膜形成用組成物、及び下層膜、並びに、レジストパターン形成方法、及び回路パターン形成方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR820000624B1 (ko) * 1977-12-15 1982-04-19 쟝-클로드 꽁발뒤으 α-아미노산의 제조방법

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR820000624B1 (ko) * 1977-12-15 1982-04-19 쟝-클로드 꽁발뒤으 α-아미노산의 제조방법

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
HERRERA, RAQUEL P. ET AL.: "Phase Transfer Catalyzed Enantioselective Strecker Reactions of a-Amino Sulfones with Cyanohydrins.", J. ORG. CHEM., vol. 71, 2006, pages 9869 - 9872 *
LEE, JI WOONG ET AL.: "Bis-Terminal Hydroxy Polyethers as All-Purpose, Multifunctional Organic Promoters: A Mechanistic Investigation and Applicaiton.", ANGEW. CHEM. INT. ED., vol. 48, 2009, pages 7683 - 7686 *
OOI, TAKASHI ET AL.: "Asymmetric Strecker Reaction of Aldimines Using Aqueous Potassium Cyanide by Phase-Transfer Catalysis of Chiral Quaternary Ammonium Salts with a Tetranaphthyl Backbone.", J. AM. CHEM. SOC., vol. 128, 2006, pages 2548 - 2549 *

Also Published As

Publication number Publication date
WO2012153991A2 (fr) 2012-11-15
KR20120127276A (ko) 2012-11-21
KR101430116B1 (ko) 2014-08-14

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