WO2006130437A2 - 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

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Publication number
WO2006130437A2
WO2006130437A2 PCT/US2006/020324 US2006020324W WO2006130437A2 WO 2006130437 A2 WO2006130437 A2 WO 2006130437A2 US 2006020324 W US2006020324 W US 2006020324W WO 2006130437 A2 WO2006130437 A2 WO 2006130437A2
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WO
WIPO (PCT)
Prior art keywords
cyano
racemic
chiral
prochiral
ester
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PCT/US2006/020324
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English (en)
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WO2006130437A3 (fr
Inventor
Li Deng
Hongming Li
Yi Wang
Fanghui Wu
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Brandeis University
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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

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    • 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

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  • 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 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

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

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Cited By (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
JP2011523654A (ja) * 2008-06-05 2011-08-18 ディーエスエム アイピー アセッツ ビー．ブイ． （４ｓ，５ｒ）−ハーフエステルの調製方法
US10752640B2 (en) 2014-08-01 2020-08-25 Nuevolution A/S Compounds active towards bromodomains

Families Citing this family (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
JP6064062B2 (ja) 2013-03-15 2017-01-18 ファイザー・インク Ａｍｐｋを活性化させるインダゾール化合物

Citations (1)

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WO2003018549A2 (fr) * 2001-08-30 2003-03-06 Chemocentryx, Inc. Composes bicycliques servant d'inhibiteurs de chimiokine se fixant a l'us28

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WO2003018549A2 (fr) * 2001-08-30 2003-03-06 Chemocentryx, Inc. Composes bicycliques servant d'inhibiteurs de chimiokine se fixant a l'us28

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Cited By (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
JP2011523654A (ja) * 2008-06-05 2011-08-18 ディーエスエム アイピー アセッツ ビー．ブイ． （４ｓ，５ｒ）−ハーフエステルの調製方法
US10752640B2 (en) 2014-08-01 2020-08-25 Nuevolution A/S Compounds active towards bromodomains

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WO2006130437A3 (fr) 2007-05-03

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