[go: up one dir, main page]

WO2006130437A3 - Reactions asymetriques formatrices de liaison carbone-carbone catalysees par des alcaloides quinquina bifonctionnels - Google Patents

Reactions asymetriques formatrices de liaison carbone-carbone catalysees par des alcaloides quinquina bifonctionnels Download PDF

Info

Publication number
WO2006130437A3
WO2006130437A3 PCT/US2006/020324 US2006020324W WO2006130437A3 WO 2006130437 A3 WO2006130437 A3 WO 2006130437A3 US 2006020324 W US2006020324 W US 2006020324W WO 2006130437 A3 WO2006130437 A3 WO 2006130437A3
Authority
WO
WIPO (PCT)
Prior art keywords
certain embodiments
quinidine
quinine
nucleophile
carbon
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.)
Ceased
Application number
PCT/US2006/020324
Other languages
English (en)
Other versions
WO2006130437A2 (fr
Inventor
Li Deng
Hongming Li
Yi Wang
Fanghui Wu
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.)
Brandeis University
Original Assignee
Brandeis University
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 claimed from US11/140,574 external-priority patent/US7312335B2/en
Application filed by Brandeis University filed Critical Brandeis University
Priority to JP2008513730A priority Critical patent/JP2008545704A/ja
Publication of WO2006130437A2 publication Critical patent/WO2006130437A2/fr
Publication of WO2006130437A3 publication Critical patent/WO2006130437A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • 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
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0237—Amines
    • 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
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • 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
    • 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
    • B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
    • B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
    • 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
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Un aspect de cette invention concerne des catalyseurs à base de quinine et de quinidine. Dans certains modes de réalisation, les catalyseurs à base de quinine et de quinidine contiennent un groupe hydroxy en position 6'. Dans d'autres modes de réalisation, les catalyseurs à base de quinine et de quinidine contiennent un groupe O-aryle ou un groupe O-aroyle en position C9. Dans d'autres modes de réalisation, les catalyseurs à base de quinine et de quinidine contiennent un groupe O-diazène éventuellement substitué ou un groupe O-benzoyle éventuellement substitué en position C9. Dans d'autres modes de réalisation encore, les catalyseurs à base de quinine et de quinidine contiennent une thiourée en position C9. Dans d'autres modes de réalisation enfin, les catalyseurs à base de quinine et de quinidine contiennent un groupe NH(=S)NH-aryle en position C9. Un autre aspect de cette invention concerne un procédé de préparation d'un composé non racémique chiral, à partir d'un alcène déficient en électron prochiral ou d'une imine prochirale, ce procédé comprenant les étapes consistant à faire réagir un alcène prochiral ou une imine prochirale avec un nucléophile en présence d'un catalyseur, produisant ainsi un composé non racémique chiral, ce catalyseur étant une quinine ou quinidine dérivée. Dans certains modes de réalisation, le nucléophile est un malonate ou un ß-cétoester. Dans d'autres modes de réalisation, le nucléophile est un alkyle ou aryle ou aralkyle 2-cyano-2-alkylacétate. Dans d'autres modes de réalisation encore, le nucléophile est un alkyle ou aryle ou aralkyle 2-cyano-2-aryleacétate. Un autre aspect de cette invention concerne un procédé de résolution cinétique comprenant l'étape consistant à faire réagir un aldéhyde racémique ou une cétone racémique avec un nucléophile en présence d'une quinine ou quinidine dérivée, ce qui permet de produire un composé chiral non racémique. Dans certains modes de réalisation, la résolution cinétique est dynamique.
PCT/US2006/020324 2005-05-27 2006-05-26 Reactions asymetriques formatrices de liaison carbone-carbone catalysees par des alcaloides quinquina bifonctionnels Ceased WO2006130437A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2008513730A JP2008545704A (ja) 2005-05-27 2006-05-26 二官能性シンコナアルカロイドにより触媒作用が及ぼされる非対照炭素−炭素結合形成反応

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US11/140,574 2005-05-27
US11/140,574 US7312335B2 (en) 2004-06-03 2005-05-27 Asymmetric Michael and Aldol additions using bifunctional cinchona-alkaloid-based catalysts
US74210205P 2005-12-02 2005-12-02
US60/742,102 2005-12-02

Publications (2)

Publication Number Publication Date
WO2006130437A2 WO2006130437A2 (fr) 2006-12-07
WO2006130437A3 true WO2006130437A3 (fr) 2007-05-03

Family

ID=36972839

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/020324 Ceased WO2006130437A2 (fr) 2005-05-27 2006-05-26 Reactions asymetriques formatrices de liaison carbone-carbone catalysees par des alcaloides quinquina bifonctionnels

Country Status (1)

Country Link
WO (1) WO2006130437A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8889730B2 (en) 2012-04-10 2014-11-18 Pfizer Inc. Indole and indazole compounds that activate AMPK
US9394285B2 (en) 2013-03-15 2016-07-19 Pfizer Inc. Indole and indazole compounds that activate AMPK

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008163022A (ja) * 2006-12-20 2008-07-17 Brandeis Univ シンコナアルカロイド触媒不斉マンニッヒ反応
US20110137046A1 (en) * 2008-06-05 2011-06-09 Fen-Er Chen Preparation method of (4s,5r)-semiester
RU2743074C2 (ru) 2014-08-01 2021-02-15 Нуэволюшон А/С Соединения, активные по отношению к бромодоменам

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003018549A2 (fr) * 2001-08-30 2003-03-06 Chemocentryx, Inc. Composes bicycliques servant d'inhibiteurs de chimiokine se fixant a l'us28

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003018549A2 (fr) * 2001-08-30 2003-03-06 Chemocentryx, Inc. Composes bicycliques servant d'inhibiteurs de chimiokine se fixant a l'us28

Non-Patent Citations (13)

* Cited by examiner, † Cited by third party
Title
BRUNNER, HENRI ET AL: "Asymmetric catalysis, 131. Naproxen derivatives by enantioselective decarboxylation", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY ( 2000 ), (11), 2119-2133 CODEN: EJOCFK; ISSN: 1434-193X, 2000, XP002399851 *
BRUNNER, HENRI ET AL: "Asymmetric catalysis, 152. .alpha.-amino acid derivatives by enantioselective decarboxylation", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY ( 2003 ), (15), 2854-2862 CODEN: EJOCFK; ISSN: 1434-193X, 2003, XP002399850 *
LI H ET AL: "Stereocontrolled creation of adjacent quaternary and tertiary stereocenters by a catalytic conjugate addition", ANGEWANDTE CHEMIE, WILEY-VCH, WEINHEIM, DE, vol. 44, no. 1, 26 November 2004 (2004-11-26), pages 105 - 108, XP002344994, ISSN: 1433-7851 *
LI, BANG-JING ET AL: "Asymmetric Michael addition of arylthiols to .alpha.,.beta.-unsaturated carbonyl compounds catalyzed by bifunctional organocatalysts", SYNLETT , (4), 603-606 CODEN: SYNLES; ISSN: 0936-5214, 22 February 2005 (2005-02-22), XP002399853 *
LI, HAO ET AL: "Organocatalytic enantioselective Michael addition of thioacetic acid to enones", TETRAHEDRON LETTERS , 47(18), 3145-3148 CODEN: TELEAY; ISSN: 0040-4039, 10 May 2006 (2006-05-10), XP002399859 *
LIU, TIAN-YU ET AL: "Enantioselective construction of quaternary carbon centre catalyzed by bifunctional organocatalyst", ORGANIC & BIOMOLECULAR CHEMISTRY , 4(11), 2097-2099 CODEN: OBCRAK; ISSN: 1477-0520, 9 May 2006 (2006-05-09), XP002399858 *
MA, DAWEI ET AL: "Diastereoselective Henry reactions of N,N-dibenzyl .alpha.-amino aldehydes with nitromethane catalyzed by enantiopure guanidines", TETRAHEDRON LETTERS ( 2002 ), 43(51), 9401-9403 CODEN: TELEAY; ISSN: 0040-4039, 2002, XP002399848 *
MCCOOEY, SEAMUS H. ET AL: "Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: inversion of configuration at C9 dramatically improves catalyst performance", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION , 44(39), 6367-6370 CODEN: ACIEF5; ISSN: 1433-7851, 1 September 2005 (2005-09-01), XP002399854 *
ROGERS, LOUIS M.-A. ET AL: "Enantioselective decarboxylation-reprotonation of an .alpha.-amino malonate derivative as a route to optically enriched cyclic .alpha.-amino acid", TETRAHEDRON LETTERS ( 2003 ), 44(15), 3047-3050 CODEN: TELEAY; ISSN: 0040-4039, 2003, XP002399849 *
SONG, JUN ET AL: "The Mannich Reaction of Malonates with Simple Imines Catalyzed by Bifunctional Cinchona Alkaloids: Enantioselective Synthesis of .beta.-Amino Acids", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 128(18), 6048-6049 CODEN: JACSAT; ISSN: 0002-7863, 18 April 2006 (2006-04-18), XP002399857 *
TILLMAN, A. LOUISE ET AL: "Direct enantio- and diastereoselective Mannich reactions of malonate and .beta.-keto esters with N-Boc and N-Cbz aldimines catalyzed by a bifunctional cinchonine derivative", CHEMICAL COMMUNICATIONS (CAMBRIDGE, UNITED KINGDOM) , (11), 1191-1193 CODEN: CHCOFS; ISSN: 1359-7345, 1 February 2006 (2006-02-01), XP002399856 *
VAKULYA, BENEDEK ET AL: "Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts", ORGANIC LETTERS , 7(10), 1967-1969 CODEN: ORLEF7; ISSN: 1523-7060, 14 April 2005 (2005-04-14), XP002399852 *
YE, JINXING ET AL: "Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives", CHEMICAL COMMUNICATIONS (CAMBRIDGE, UNITED KINGDOM) , (35), 4481-4483 CODEN: CHCOFS; ISSN: 1359-7345, 8 August 2005 (2005-08-08), XP002399855 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8889730B2 (en) 2012-04-10 2014-11-18 Pfizer Inc. Indole and indazole compounds that activate AMPK
US9394285B2 (en) 2013-03-15 2016-07-19 Pfizer Inc. Indole and indazole compounds that activate AMPK

Also Published As

Publication number Publication date
WO2006130437A2 (fr) 2006-12-07

Similar Documents

Publication Publication Date Title
De Vos et al. Chiral catalyst immobilization and recycling
Yamashita et al. Catalytic enantioselective aldol reactions
Wang et al. Catalytic enantioselective intermolecular desymmetrization of 3-substituted oxetanes.
Shibasaki et al. Lanthanide complexes in multifunctional asymmetric catalysis
WO2009094201A3 (fr) Catalyseurs pour des réactions de métathèse comprenant la métathèse énantiosélective d'oléfines et procédés correspondants
BR0313814A (pt) Processo para preparação de aldeìdos por hidroformilação de compostos olefinicamente insaturados, catalisado por complexos metálicos não modificados, na presença de ésteres de ácido carbÈnico cìclicos
BR9910837B1 (pt) catalisador para produção de acetato de vinila por reação de etileno, oxigênio e ácido acético e método para preparar um catalisador.
EP1180511A4 (fr) Procede de preparation d'esters de formate ou de methanol et catalyseur destine a cet effet
Matzel et al. Synthesis of β‐chiral amines by dynamic kinetic resolution of α‐branched aldehydes applying imine reductases
WO2004052896A8 (fr) Procede pour produire des complexes metalliques
WO2006130437A3 (fr) Reactions asymetriques formatrices de liaison carbone-carbone catalysees par des alcaloides quinquina bifonctionnels
FR2914927B1 (fr) Procede de fabrication d'esters alcooliques a partir de triglycerides et d'alcools au moyens de catalyseurs heterogenes a base de phosphate ou de compose organophosphore d'un metal du groupe 4.
Park et al. Catalytic enantioselective fluorination of α-cyano esters by phase-transfer catalysis using chiral quaternary ammonium salts
DE60116295D1 (de) Verfahren zur herstellung chiraler verbindungen aus racemischen epoxiden unter verwendung von chiralen salenkatalysatoren
ATE490953T1 (de) Verfahren zur herstellung von hydroxytyrosol
EP2275529A3 (fr) Procédé de préparation d'aspartate et d'acides aminés dérivés utilisant un microorganisme doté d'un shunt glyoxylique amélioré
Fukuchi et al. Catalytic asymmetric aldol reactions of enolizable carbon pronucleophiles with formaldehyde and ethyl glyoxylate
DE602004010711D1 (de) Verfahren zur katalytischen herstellung von hydrocodon und hydromorphon
WO2008142333A3 (fr) Procede de synthese de catalyseurs heterogenes au palladium, catalyseurs obtenus et utilisations de ces derniers
Uraguchi et al. Enantioselective protonation of α-hetero carboxylic acid-derived ketene disilyl acetals under chiral ionic Brønsted acid catalysis
JP2004505098A5 (fr)
Rohit et al. Recent Advances in the Creation of Asymmetric Carbon Centre (s) by Generation of Carbon‐Heteroatom Bond (s) Using Metal‐Pybox Complexes
ATE376550T1 (de) Katalytisches verfahren zur herstellung von hydromorphone und hydrocodone
WO2007127415A8 (fr) Procédé de production de polyoléfines utilisant des catalyseurs à base de métal de transition fluorés à faible ph
EP1724251A4 (fr) Procede pour la fabrication de composes hydroxymethyles optiquement actifs

Legal Events

Date Code Title Description
ENP Entry into the national phase

Ref document number: 2008513730

Country of ref document: JP

Kind code of ref document: A

121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

NENP Non-entry into the national phase

Ref country code: RU

122 Ep: pct application non-entry in european phase

Ref document number: 06771227

Country of ref document: EP

Kind code of ref document: A2