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Cinchona alkali ligand and preparation method and application thereof

A technology of cinchona base and ligands, which is applied in the field of cinchona base ligands and their preparation, can solve the problems of general reaction catalytic effect and achieve high ee value and yield

Active Publication Date: 2021-12-24
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the substituents on the previously synthesized ligand phosphorus are all commercial aryl or alkyl groups, there are limitations in structure, and the catalytic effect for other types of reactions is general.

Method used

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  • Cinchona alkali ligand and preparation method and application thereof
  • Cinchona alkali ligand and preparation method and application thereof
  • Cinchona alkali ligand and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～13

[0093] Embodiments 1 to 13 are applicable to the following synthetic routes, and the steps refer to the general synthetic methods

[0094]

Embodiment 1

[0096]

[0097] 1 H NMR (400MHz, CDCl 3 )δ8.76(d,J=4.6Hz,1H),8.08(d,J=9.2Hz,1H),7.90–7.73(m,4H),7.65–7.38(m,9H),7.25(s,8H ),7.07(s,4H),5.68(ddd,J=17.5,10.3,7.4Hz,1H),5.53(s,1H),4.95(dd,J=13.7,10.2Hz,2H),4.00(s, 3H), 3.22(d, J=14.9Hz, 1H), 3.12–2.86(m, 2H), 2.73–2.51(m, 1H), 2.43(s, 24H), 2.24(q, J=6.9Hz, 2H ), 1.74–1.50 (m, 3H), 1.42 (t, J=12.1Hz, 1H), 1.02 (dd, J=14.3, 6.6Hz, 1H). 31 P NMR (162MHz, CDCl 3 )δ-9.1.

Embodiment 2

[0099]

[0100] 1 H NMR (400MHz, CDCl 3 )δ8.72(d, J=4.5Hz, 1H), 8.08(d, J=9.2Hz, 1H), 7.88(d, J=12.6Hz, 2H), 7.78(d, J=9.8Hz, 2H) ,7.64(d,J=7.5Hz,2H),7.59–7.40(m,18H),7.35–7.30(m,1H),5.73–5.56(m,1H),5.49(s,1H),4.88(t ,J=14.1Hz,2H),3.98(s,3H),3.14(s,1H),3.07–2.87(m,2H),2.65–2.38(m,2H),2.29–2.16(m,1H), 1.62 (d, J=34.6Hz, 4H), 1.47–1.36 (m, 72H), 1.04 (dd, J=14.1, 6.5Hz, 1H). 31 P NMR (162MHz, CDCl 3 ) δ-10.3.

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Abstract

The invention belongs to the field of organic chemical ligands, and particularly relates to a cinchona alkali ligand, which has a structure shown in a general formula I or a tautomer, an enantiomer and a diastereoisomer thereof, in the formula I, R1 is selected from alkyl, alkenyl and -CH = CHPh, R2 is selected from hydrogen, alkyl, phenyl and substituted phenyl, and R is selected from substituted phenyl. The invention also discloses a preparation method and application of the cinchona alkaloid ligand. The ligand disclosed by the invention has advantages in stereoselectivity and reaction efficiency, and a higher ee value and yield can be obtained in an asymmetric reaction.

Description

technical field [0001] The invention belongs to the field of organic chemical ligands, in particular to a cinchona base ligand and its preparation method and application. Background technique [0002] As an important class of natural chiral products, cinchonaine (quinine) and its analogues widely exist in nature. Based on its complex spatial structure and multiple coordination sites, it has been used in asymmetric reactions catalyzed by small organic molecules. In recent years, with the rapid development of the field of transition metal asymmetric catalysis, the demand for various new chiral ligand frameworks is increasing. The nitrogen, nitrogen, and phosphorus ligands derived from quinine and its analogs contain a tertiary amine, a trivalent phosphorus, and an amide structure (which can be deprotonated under the action of a base to generate an amide anion). This type of ligand can not only provide Hydrogen bonding and other effects can also coordinate with transition met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6561C07F1/08B01J31/24
CPCC07F9/65615C07F1/08B01J31/2409B01J2531/16B01J2231/4277
Inventor 刘心元张宇峰李忠良顾强帅
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA