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Catalyst and reaction process

Foreign code F110003815
File No. E07615WO
Posted date Jul 5, 2011
Country United States of America
Application number 86505309
Gazette No. 20110054190
Gazette No. 8222177
Date of filing Jan 28, 2009
Gazette Date Mar 3, 2011
Gazette Date Jul 17, 2012
International application number JP2009051322
International publication number WO2009096409
Date of international filing Jan 28, 2009
Date of international publication Aug 6, 2009
Priority data
  • P2008-015906 (Jan 28, 2008) JP
  • 2009WO-JP51322 (Jan 28, 2009) WO
Title Catalyst and reaction process
Abstract (US8222177)
Disclosed is a technology for enabling an efficient asymmetric Michael addition reaction which does not require a large amount of a malonic ester, while having a short reaction time.
Specifically disclosed is a catalyst which is composed of MX2 (wherein M is Be, Mg, Ca, Sr, Ba or Ra and X is an arbitrary group) and a compound represented by general formula [I]. [In the formula, R7, R8, R9 and R10 each represents a substituted cyclic group or an unsubstituted cyclic group.]
Scope of claims [claim1]
1. A reaction method, comprising reacting a compound represented by formula [II] with a compound represented by formula [III] in the presence of a catalyst configured using MX2 and a compound represented by formula [I], to form a compound of formula [IV]:
wherein:
R1, R2, R3 and R4 individually represent a H or a hydrocarbon;
W1, W2 and W3 individually represent an electron-withdrawing group selected from the group consisting of an ester group, a carboxyl group, a carbonyl group, a nitrile group and a nitro group;
M is Sr;
X is an alkoxide group, an amide group, or a hexamethyldisilazide group; and
R7, R8, R9, and R10 each represents a substituted cyclic group or a unsubstituted cyclic group and wherein optionally R9 and R10 form a ring.
[claim2]
2. A reaction method according to claim 1, wherein said MX2 is M(OR5)2 wherein M is Sr and R5 is an alkyl group.
[claim3]
3. A reaction method according to claim 1, wherein said MX2 is Sr(OR5)2 and R5 is an alkyl group having a carbon number of 1 to 10.
[claim4]
4. A reaction method according to claim 1, wherein said X is an amide group.
[claim5]
5. A reaction method according to claim 1, wherein said X is hexamethyldisilazide.
[claim6]
6. A reaction method according to claim 1, wherein said cyclic group is an aromatic group.
[claim7]
7. A reaction method according to claim 1, wherein the compound represented by said general formula [I] and M of said compound MX2 are coordinate-bonded to each other.
[claim8]
8. A reaction method according to claim 1, wherein said electron-withdrawing group is an ester group or a carbonyl group.
[claim9]
9. A reaction method according to claim 1, wherein the compound represented by said general formula [II] is a dicarboxylate ester.
[claim10]
10. A reaction method according to claim 1, wherein the compound represented by said general formula [II] is a malonic ester.
[claim11]
11. A reaction method according to claim 1, wherein the compound represented by said general formula [III] is an enone.
[claim12]
12. A reaction method according to claim 1, wherein an aromatic hydrocarbon solvent is used as a solvent of said reaction.
  • Inventor, and Inventor/Applicant
  • KOBAYASHI SHU
  • AGOSTINHO MAGNO
  • SCHNEIDER UWE
  • YAMAGUCHI MIYUKI
  • 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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