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Method for manufacturing an optically active hydroxymethylated compound and a catalyst therefore

Foreign code F110003812
File No. E07612WO
Posted date Jul 5, 2011
Country United States of America
Application number 79552506
Gazette No. 20080139835
Gazette No. 7541307
Date of filing Jan 27, 2006
Gazette Date Jun 12, 2008
Gazette Date Jun 2, 2009
International application number JP2006301293
International publication number WO2006080425
Date of international filing Jan 27, 2006
Date of international publication Aug 3, 2006
Priority data
  • P2005-022643 (Jan 31, 2005) JP
  • 2006WO-JP301293 (Jan 27, 2006) WO
Title Method for manufacturing an optically active hydroxymethylated compound and a catalyst therefore
Abstract (US7541307)
A silicon enolate represented by the following formula (Formula 1) (in the formula, R5 to R7 represent hydrogen atoms, aliphatic hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, monocyclic or polycyclic aromatic or aromatic-aliphatic hydrocarbon groups or heterocyclic groups, R5 and R7 are different, R6 is not a hydrogen atom, each R8 may be identical or different and represents a methyl group, ethyl group or isopropyl group) and formaldehyde are allowed to react in an aqueous solution or a mixed solvent of water and an organic solvent in the presence of a catalyst obtained by mixing a ligand comprising a chiral bipyridine compound or its antipode and Bi(OTf)3.
Scope of claims [claim1]
1. A method for manufacturing an optically active hydroxymethylated compound that allows a silicon enolate represented by the following formula (Formula 1)
(in the formula, R5 to R7 represent hydrogen atoms, aliphatic hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, monocyclic or polycyclic aromatic or aromatic-aliphatic hydrocarbon groups or heterocyclic groups, R5 and R7 are different, R6 is not a hydrogen atom, each R8 may be identical or different and represents a methyl group, ethyl group or isopropyl group) and formaldehyde to react in an aqueous solution or in a mixed solvent of water and an organic solvent or in a mixed solvent of water and organic solvents in the presence of a catalyst obtained by blending a ligand comprising a chiral bipyridine compound or its antipode and a Lewis acid represented by BiY3 (in the formula, Y represents a halogen atom, OAc, OCOCF3, ClO4, SbF6, PF6 or OSO2CF3).
[claim2]
4. A catalyst obtained by mixing a ligand comprising a chiral bipyridine compound or its antipode and Bi(OTf)3.
[claim3]
2. A method described in claim 1 wherein said ligand comprising the chiral bipyridine compound is represented by the following formula (Chemical Formula 2)
(in the formula R1 represents an alkyl group with four or fewer carbon atoms or a phenyl group).
[claim4]
3. The method described in claim 1 wherein the molar ratio represented by (said ligand comprising the chiral bipyridine compound or its antipode/said Lewis acid) is at least 2.5.
[claim5]
5. The method described in claim 2, wherein the molar ratio represented by (said ligand comprising the chiral bipyridine compound or its antipode/said Lewis acid) is at least 2.5.
[claim6]
6. The method described in claim 1, wherein a 2,2'-bipyridine is also added as an additive.
[claim7]
7. The method described in claim 2, wherein a 2,2'-bipyridine is also added as an additive.
[claim8]
8. The method described in claim 3, wherein a 2,2'-bipyridine is also added as an additive.
  • Inventor, and Inventor/Applicant
  • KOBAYASHI SHU
  • MANABE KEI
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
IPC(International Patent Classification)
Reference ( R and D project ) ERATO KOBAYASHI Highly Functionalized Reaction Environments AREA
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