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Catalyst and michael addition reaction process

Foreign code F110003953
File No. E07615WO
Posted date Jul 7, 2011
Country EPO
Application number 09705661
Gazette No. 2258477
Gazette No. 2258477
Date of filing Jan 28, 2009
Gazette Date Dec 8, 2010
Gazette Date Mar 25, 2015
International application number JP2009051322
International publication number WO2009096409
Date of international filing Jan 28, 2009
Date of international publication Aug 6, 2009
Priority data
  • 2009JP051322 (Jan 28, 2009) WO
  • P2008-015906 (Jan 28, 2008) JP
Title Catalyst and michael addition reaction process
Abstract 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 MX 2 (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, R 7 , R 8 , R 9 and R 10 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 the following general formula [II] with a compound represented by the following general formula [III] in the presence of a catalyst configured using MX 2 wherein M is Mg, Ca, Sr, or Ba, and X is OR **5 or an amide group, wherein R **5 is an alkyl group, and a compound represented by the following general formula [I]: (see diagramm) wherein R **7, R **8, R **9, and R **10 each represents a substituted cyclic group or a unsubstituted cyclic group and there are two cases for R **9 and R **10, i.e. the case that they form a ring and the case that they do not form a ring, (see diagramm)(see diagramm) wherein each of R **1, R **2, R **3, and R **4 is an arbitrary substituent and each of W **1, W **2, and W **3 is an electron-withdrawing group,
said reaction method being used for obtaining a compound represented by the following general formula [IV]: (see diagramm) wherein each of R **1, R **2, R **3, and R **4 is an arbitrary substituent, and each of W **1, W **2, and W **3 is an electron withdrawing group.
[claim2]
2. A reaction method according to claim 1, wherein an aromatic hydrocarbon solvent is used as a solvent of said reaction.
[claim3]
3. Use of a catalyst for catalyzing a reaction between a compound represented by the following general formula [II] and a compound represented by the following general formula [III] said catalyst configured using MX 2 wherein M is Mg, Ca, Sr, or Ba, and X is OR **5 or an amide group, wherein R **5 is an alkyl group, and a compound represented by the following general formula [I]: (see diagramm) wherein R **7, R **8, R **9, and R **10 each represents a substituted cyclic group or a unsubstituted cyclic group and there are two cases for R **9 and R **10, i.e. the case that they form a ring and the case that they do not form a ring, (see diagramm)(see diagramm) wherein each of R **1, R **2, R **3, and R **4 is an arbitrary substituent and each of W **1, W **2, and W **3 is an electron-withdrawing group.
[claim4]
4. A catalyst configured using MX 2 wherein M is Ca, Sr, or Ba , and X is OR **5 or an amide group, wherein R **5 is an alkyl group, and a compound represented by the following general formula [I]: (see diagramm) wherein R **7, R **8, R **9, and R **10 each represents a substituted cyclic group or a unsubstituted cyclic group and there are two cases for R **9 and R **10, i.e. the case that they form a ring and the case that they do not form a ring.
[claim5]
5. A catalyst according to claim 4, wherein said MX 2 is M(OR **5) 2 wherein M is Ca, Sr or Ba and R **5 is an alkyl group having a carbon number of 1 to 10.
[claim6]
6. A catalyst according to claim 4, wherein said MX 2 is Sr(OR **5) 2 and wherein R **5 is an alkyl group having a carbon number of 1 to 10.
[claim7]
7. A catalyst according to claim 4, wherein said X is hexamethyldisilazide.
[claim8]
8. A catalyst according to claim 4, wherein said cyclic group is an aromatic group.
[claim9]
9. A catalyst according to one of claim 4 to claim 8, wherein the compound represented by said general formula [I] and M of said compound MX 2 are coordinate-bonded to each other.
[claim10]
10. A reaction method according to claim 1, wherein said MX 2 is M(OR **5) 2 wherein M is Ca, Sr or Ba and R **5 is an alkyl group having a carbon number of 1 to 10.
[claim11]
11. A reaction method according to claim 1, wherein said MX 2 is Sr(OR **5) 2 and wherein R **5 is an alkyl group having a carbon number of 1 to 10.
[claim12]
12. A reaction method according to claim 1, wherein said X is hexamethyldisilazide.
[claim13]
13. A reaction method according to claim 1, wherein said cyclic group is an aromatic group.
[claim14]
14. A reaction method according to claim 1 or one of claims 10 to 13, wherein the compound represented by said general formula [I] and M of said compound MX 2 are coordinate-bonded to each other.
[claim15]
15. A reaction method according to claim 1, wherein each of said R **1, R **2, R **3, and R **4 is an H group or a hydrocarbon group.
[claim16]
16. A reaction method according to claim 1, wherein said electron-withdrawing group is an ester group or a carbonyl group.
[claim17]
17. A reaction method according to claim 1, wherein the compound represented by said general formula [II] is a dicarboxylate ester.
[claim18]
18. A reaction method according to claim 1, wherein the compound represented by said general formula [II] is a malonic ester.
[claim19]
19. A reaction method according to claim 1, wherein the compound represented by said general formula [III] is an enone.
  • Applicant
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • Inventor
  • KOBAYASHI SHU
  • AGOSTINHO MAGNO
  • SCHNEIDER UWE
  • YAMAGUCHI MIYUKI
IPC(International Patent Classification)
Reference ( R and D project ) ERATO KOBAYASHI Highly Functionalized Reaction Environments AREA
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