Title:
DE-C2-SYMMETRIC DIPHENYLAMINE-TYPE CHIRAL BISOXAZOLINE LIGAND, SYNTHESIS METHOD THEREFOR AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2020/238559
Kind Code:
A1
Abstract:
Disclosed are a de-C2-symmetric diphenylamine-type chiral bisoxazoline ligand as shown in formula 3, a synthesis method therefor and the use thereof in an asymmetric catalytic reaction. The C2-symmetry of the ligand is removed by introducing different groups on a diphenylamine skeleton, achieving precise regulation for the "electronic effect" of the ligand skeleton. Such ligands result in the compound as shown in formula 1 using an o-aminobenzoic acid derivative and an o-chlorobenzoic acid derivative as starting raw materials, next same is reacted with a chiral amino alcohol compound as shown in formula 4 so as to obtain the compound β-bishydroxyamide as shown in formula 2, and then, the β-bishydroxyamide is condensed to prepare the compound de-C2-symmetric diphenylamine-type chiral bisoxazoline ligand as shown in formula 3. In addition, also provided is the use of the de-C2-symmetric diphenylamine-type chiral bisoxazoline ligand with a catalyst, formed by coordinating with a copper salt, a zinc salt, a nickel salt, an iron salt or a rhodium salt, in an asymmetric catalytic reaction.
More Like This:
Inventors:
XU DANQIAN (CN)
WANG YIFENG (CN)
WANG BIAO (CN)
XU ZHENYUAN (CN)
WANG YIFENG (CN)
WANG BIAO (CN)
XU ZHENYUAN (CN)
Application Number:
PCT/CN2020/088254
Publication Date:
December 03, 2020
Filing Date:
April 30, 2020
Export Citation:
Assignee:
UNIV ZHEJIANG TECHNOLOGY (CN)
International Classes:
C07D263/14; B01J31/22; C07B53/00; C07C67/307; C07C67/313; C07C69/757; C07C69/76; C07C331/14; C07D209/10; C07D263/10; C07D307/85
Foreign References:
| CN110229114A | 2019-09-13 | |||
| CN110204468A | 2019-09-06 | |||
| CN108822036A | 2018-11-16 | |||
| JP2018172644A | 2018-11-08 | |||
| CN108774127A | 2018-11-09 |
Other References:
WANG BIAO ET AL.: "Asymmetric fluorination of indanone-2-carboxylates using a polystyrene-supported diphenylamine-linked bis(oxazoline) complex", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 16, no. 41, 28 September 2018 (2018-09-28), XP055762919, ISSN: 1477-0520, DOI: 20200717213711X
XIONG YANG: "Enantioselective 1, 2-Difunctionalization of 1, 3-Butadiene by Sequential Alkylation and Carbonyl Allylation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 140, no. 8, 8 February 2018 (2018-02-08), XP055762918, ISSN: 0002-7863, DOI: 20200717220859X
LIU HAN ET AL.: "Immobilization of Diphenylamine-Linked Bis(oxazoline) Ligands and Their Application in the Asymmetric Friedel-Crafts Alkylation of Indole Derivatives with Nitroalkenes", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no. 11,, 4 March 2010 (2010-03-04), XP055762917, ISSN: 1434-193X
LIU HAN ET AL.: "Immobilization of Diphenylamine-Linked Bis(oxazoline) Ligands and Their Application in the Asymmetric Friedel-Crafts Alkylation of Indole Derivatives with Nitroalkenes", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no. 11,, 4 March 2010 (2010-03-04), XP055762917, ISSN: 1434-193X
LIU HAN ET AL.: "Modification of diphenylamine-linked bis(oxazoline) ligands: Tuning of electronic effect and rigidity of ligand skeleton", SCIENCE IN CHINA, SERIES B: CHEMISTRY, vol. 52, no. 9, 30 September 2009 (2009-09-30), XP055700602, ISSN: 1006-9291
LIU HAN ET AL.: "Modification of diphenylamine-linked bis(oxazoline) ligands: Tuning of electronic effect and rigidity of ligand skeleton", SCIENCE IN CHINA, SERIES B: CHEMISTRY, vol. 52, no. 9, 30 September 2009 (2009-09-30), XP055700602, ISSN: 1006-9291
LIU HAN ET AL.: "Asymmetric Friedel-Crafts alkylation of methoxyfuran with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline)-Zn(II) complexes", ORGANIC LETTERS, vol. 23, no. 9, 30 September 2007 (2007-09-30), XP055762916, ISSN: 1523-7060, DOI: 20200717232257X
GOODELL JOHN R. ET AL.: "Synthesis and evaluation of acridine- and acridone-based anti-herpes agents with topoisomerase activity", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 14, no. 16, 19 May 2006 (2006-05-19), XP027992817, ISSN: 0968-0896, DOI: 20200717233523Y
CHU JOHN C. K. ET AL.: "Zn-Catalyzed Enantio- and Diastereoselective Formal [4 + 2] Cycloaddition Involving Two Electron-Deficient Partners: Asymmetric Synthesis of Piperidines from 1-Azadienes and Nitro-Alkenes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 137, no. 13, 30 March 2015 (2015-03-30), XP055762915, ISSN: 0002-7863, DOI: 20200717223212A
XIONG YANG: "Enantioselective 1, 2-Difunctionalization of 1, 3-Butadiene by Sequential Alkylation and Carbonyl Allylation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 140, no. 8, 8 February 2018 (2018-02-08), XP055762918, ISSN: 0002-7863, DOI: 20200717220859X
LIU HAN ET AL.: "Immobilization of Diphenylamine-Linked Bis(oxazoline) Ligands and Their Application in the Asymmetric Friedel-Crafts Alkylation of Indole Derivatives with Nitroalkenes", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no. 11,, 4 March 2010 (2010-03-04), XP055762917, ISSN: 1434-193X
LIU HAN ET AL.: "Immobilization of Diphenylamine-Linked Bis(oxazoline) Ligands and Their Application in the Asymmetric Friedel-Crafts Alkylation of Indole Derivatives with Nitroalkenes", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no. 11,, 4 March 2010 (2010-03-04), XP055762917, ISSN: 1434-193X
LIU HAN ET AL.: "Modification of diphenylamine-linked bis(oxazoline) ligands: Tuning of electronic effect and rigidity of ligand skeleton", SCIENCE IN CHINA, SERIES B: CHEMISTRY, vol. 52, no. 9, 30 September 2009 (2009-09-30), XP055700602, ISSN: 1006-9291
LIU HAN ET AL.: "Modification of diphenylamine-linked bis(oxazoline) ligands: Tuning of electronic effect and rigidity of ligand skeleton", SCIENCE IN CHINA, SERIES B: CHEMISTRY, vol. 52, no. 9, 30 September 2009 (2009-09-30), XP055700602, ISSN: 1006-9291
LIU HAN ET AL.: "Asymmetric Friedel-Crafts alkylation of methoxyfuran with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline)-Zn(II) complexes", ORGANIC LETTERS, vol. 23, no. 9, 30 September 2007 (2007-09-30), XP055762916, ISSN: 1523-7060, DOI: 20200717232257X
GOODELL JOHN R. ET AL.: "Synthesis and evaluation of acridine- and acridone-based anti-herpes agents with topoisomerase activity", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 14, no. 16, 19 May 2006 (2006-05-19), XP027992817, ISSN: 0968-0896, DOI: 20200717233523Y
CHU JOHN C. K. ET AL.: "Zn-Catalyzed Enantio- and Diastereoselective Formal [4 + 2] Cycloaddition Involving Two Electron-Deficient Partners: Asymmetric Synthesis of Piperidines from 1-Azadienes and Nitro-Alkenes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 137, no. 13, 30 March 2015 (2015-03-30), XP055762915, ISSN: 0002-7863, DOI: 20200717223212A
Attorney, Agent or Firm:
TIANZHENG PATENT ATTORNEYS (CN)
Download PDF:
Previous Patent: IMAGE SUPER-RESOLUTION METHOD AND SYSTEM
Next Patent: VIDEO TARGET TRACKING METHOD AND APPARATUS, COMPUTER DEVICE AND STORAGE MEDIUM
Next Patent: VIDEO TARGET TRACKING METHOD AND APPARATUS, COMPUTER DEVICE AND STORAGE MEDIUM