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Method for determination of absolute configuration of chiral compounds achieved

Foreign code F110003827
File No. I019P001WO
Posted date Jul 5, 2011
Country United States of America
Application number 54449604
Gazette No. 20060148091
Gazette No. 7736902
Date of filing Feb 6, 2004
Gazette Date Jul 6, 2006
Gazette Date Jun 15, 2010
International application number JP2004001267
International publication number WO2004070364
Date of international filing Feb 6, 2004
Date of international publication Aug 19, 2004
Priority data
  • P2003-029190 (Feb 6, 2003) JP
  • 2004WO-JP01267 (Feb 6, 2004) WO
Title Method for determination of absolute configuration of chiral compounds achieved
Abstract (US7736902)
The present invention provides a simple, highly sensitive, and highly precise method for determining the absolute configuration of a chiral compound such as a diamine or an amino alcohol.
The present invention is directed to a method for determining the absolute configuration of an asymmetric carbon of a chiral compound on the basis of the sign of the Cotton effect by analyzing a solution containing the chiral compound and a porphyrin dimer by circular dichroism spectroscopy.
Scope of claims [claim1]
1. A method for determining the absolute configuration of an asymmetric carbon of a chiral compound on the basis of the sign of the Cotton effect by analyzing a solution containing the chiral compound and a porphyrin dimer by circular dichroism spectroscopy, wherein the porphyrin dimer:
(a) has a carbon chain-crosslinked porphyrin dimer structure,
(b) is such that one porphyrin ring of the dimer has a Zn2+ metal center and the other porphyrin ring of the dimer is a free porphyrin ring, and
(c) is such that the free porphyrin ring has a methyl group or substituent bulkier than a methyl group at one or more of the second carbons from the carbon bonded to the crosslinking carbon chain around the outer periphery of the free porphyrin ring, and
the chiral compound:
(i) is capable of coordinating to the porphyrin dimer,
(ii) has an asymmetric carbon directly bonded to a group capable of coordinating to the porphyrin dimer, or an asymmetric carbon adjacent to the carbon atom bonded to a group capable of coordinating to the porphyrin dimer, and
(iii) is a diamine or an amino alcohol.
[claim2]
2. The method according to claim 1, wherein the porphyrin dimer is a compound represented by the following formula (1):
Formula 1
wherein M2+ is Zn2+,
n is 2 or 3,
Ra to Rd are the same or different and are each a hydrogen atom or a methyl group or substituent bulkier than a methyl group,
either Rc or Rd is a methyl group or substituent bulkier than a methyl group, and
R1 to R12 are the same or different and are each a hydrogen atom or a methyl group or substituent bulkier than a methyl group.
[claim3]
3. The method according to claim 2, wherein either Rc or Rd in Formula 1 is selected from the group consisting of 1) a C1 to C8 hydrocarbon group, 2) an oxygen-containing substituent, 3) a nitrogen-containing substituent, 4) a halogen atom, and 5) a halogenated hydrocarbon group.
[claim4]
4. The method according to claim 1, wherein the porphyrin dimer is a compound represented by the following formula (2):
Formula 2.
  • Inventor, and Inventor/Applicant
  • INOUE YOSHIHISA
  • BOROVKOV VICTOR V
  • HEMBURY GUY A
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
IPC(International Patent Classification)
U.S. Cl./(Sub)
  • G01N021/19
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