Chiral metal complex and use thereof for analyzing chirality of charged compound by 1H NMR spectroscopy

Patent metadata

Field	Value
Publication number	US-9851314-B2
Application number	US-201514947538-A
Country	US
Kind code	B2
Filing date	Nov 20, 2015
Priority date	Aug 19, 2015
Publication date	Dec 26, 2017
Grant date	Dec 26, 2017

Abstract

Provided are novel ligand, a chiral metal complex including the same, and a use of the chiral metal complex for analyzing the chirality of a charged compound by 1 H NMR spectroscopy. The chiral metal complex of the present invention may be used as the chiral solvating agent to conveniently analyze the optical purity of charged compounds such as various amine derivatives, carboxylic acid derivatives, cyanohydrin derivatives and charged metal complexes by 1 H NMR spectroscopy.

First claim

What is claimed is:

1. A N 2 O 2 ligand having the following Chemical Formula 1:

wherein
R 1 and R 2 are independently of each other (C1-C10) alkyl or (C6-C20) aryl, or R 1 and R 2 are linked via (C2-C6) alkylene to form a cycloaliphatic ring; and
R 3 and R 4 are independently of each other hydrogen, (C1-C10) alkyl, or halogen.

2. The N 2 O 2 ligand of claim 1 , wherein
R 1 and R 2 are independently of each other methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, naphthyl or anthryl, or R 1 and R 2 are linked via (C3-C4) alkylene to form a cycloaliphatic ring; and
R 3 and R 4 are independently of each other hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, chloro, bromo or fluoro.

3. A metal complex having the following Chemical Formula 2:

wherein
R 1 and R 2 are independently of each other (C1-C10) alkyl or (C6-C20) aryl, or R 1 and R 2 are linked via (C2-C6) alkylene to form a cycloaliphatic ring;
R 3 and R 4 are independently of each other hydrogen, (C1-C10) alkyl, or halogen;

when M is Al 3+ or Sc 3+ , n is −1, and Y is H + , Li + , Na + , K + , Ag + , Cs + , NR 4 + , ½ Mg 2+ , ½ Ca 2+ , ½ Zn 2+ or ⅓ Al 3+ ; and
when M is Ti 4+ , n is 0, and Y does not exist.

4. The metal complex of claim 3 , wherein
R 1 and R 2 are independently of each other methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, naphthyl or anthryl, or R 1 and R 2 are linked via (C3-C4) alkylene to form a cycloaliphatic ring;
R 3 and R 4 are independently of each other hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, chloro, bromo or fluoro;
when M is Al3+ or Sc3+ , n is −1, and Y is H+ or Na+; and
when M is Ti4+, n is 0, and Y does not exist.

5. The metal complex of claim 3 , wherein it is selected from following structures:

6. A method of measuring an optical purity of a chiral analyte, comprising the steps of combining the chiral metal complex of claim 3 as a chiral solvating agent with the chiral analyte and measuring the optical purity of the chiral analyte by nuclear magnetic resonance spectroscopy.

7. The method of claim 6 , wherein the chiral metal complex is used in 0.5 to 10 equivalents relative to the chiral analyte.

Assignees

• Korea Advanced Inst Sci & Tech
• Inst Basic Science

Inventors

• Kim Hyunwoo
• SEO Min-Seob

Classifications

• G01N24/08 Primary

  by using nuclear magnetic resonance (G01N24/12 takes precedence) · CPC title

• C07F7/28

  Titanium compounds · CPC title

• C07C215/50

  with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain · CPC title

• C07F5/069

  without C-aluminium linkages · CPC title

• C07F5/003

  without C-Metal linkages · CPC title