Title:
PROCESS FOR PRODUCING OPTICALLY ACTIVE CYCLOPROPANE COMPOUND AND ASYMMETRIC COPPER COMPLEX FOR USE IN THE SAME
Document Type and Number:
WIPO Patent Application WO/2005/028413
Kind Code:
A1
Abstract:
A process for producing an optically active cyclopropane compound represented by the formula (4): (4) (wherein R3, R4, R5, and R6 are the same or different and each represents hydrogen, halogeno, (un)substituted alkyl, etc.; R7 represents C1-6 alkyl; and the asterisked carbon atom is an asymmetric carbon atom), characterized by reacting a prochiral olefin represented by the formula (2): (2) (wherein R3, R4, R5, and R6 are the same as defined above) with a diazoacetic ester represented by the formula (3): N2CHCO2R7 (3) (wherein R7 is the same as defined above) in the presence of an asymmetric copper complex prepared from an optically active cycloalkylidenebisoxazoline compound represented by the formula (1): (1) (wherein R1 represents hydrogen, C1-6 alkyl, etc., provided that two R1's may be bonded to each other to form a ring in cooperation with the carbon atom bonded thereto; R2 represents C1-6 alkyl, etc.; n is an integer of 0 to 3; and * indicates an asymmetric carbon atom) and from a copper compound.
Inventors:
ITAGAKI MAKOTO (JP)
MASUMOTO KATSUHISA (JP)
MINAMIDA RYO (JP)
MASUMOTO KATSUHISA (JP)
MINAMIDA RYO (JP)
Application Number:
PCT/JP2004/014031
Publication Date:
March 31, 2005
Filing Date:
September 17, 2004
Export Citation:
Assignee:
SUMITOMO CHEMICAL CO (JP)
ITAGAKI MAKOTO (JP)
MASUMOTO KATSUHISA (JP)
MINAMIDA RYO (JP)
ITAGAKI MAKOTO (JP)
MASUMOTO KATSUHISA (JP)
MINAMIDA RYO (JP)
International Classes:
B01J31/22; C07B53/00; C07B61/00; C07C67/347; C07C68/06; C07C69/757; C07D263/12; C07F1/00; (IPC1-7): C07C67/347; C07C69/757; C07D263/12; C07B53/00; C07B61/00; B01J31/22
Foreign References:
| JP2003012675A | 2003-01-15 |
Other References:
CHARETTE, A.B. ET AL.: "Bis(oxazoline)-copper(I)-catalyzed enantioselective cyclopropanation of cinnamate esters with diazomethane", TETRAHEDRON: ASYMMETRY, no. 14, 2003, pages 867 - 872, XP004417218
DEETH, J. ET AL.: "AMolecular Mechanics Study of Copper (II)-Cathlyzed Asymmetric Diels-Alder Reactions)", ORGANOMETALLICS, vol. 23, no. 5, 2004, pages 1042 - 1054, XP002984486
DENMARK, S.E. ET AL.: "Effect of Ligand Structure in the Bisoxazoline Mediated Asymmetric Addition of Methyllithium to Imines", J.ORG.CHEM, vol. 65, no. 18, 2000, pages 5875 - 5878, XP002984487
JOURNAL OF ORGANIC CHEMISTRY, vol. 65, 2000, pages 5875
See also references of EP 1674445A4
DEETH, J. ET AL.: "AMolecular Mechanics Study of Copper (II)-Cathlyzed Asymmetric Diels-Alder Reactions)", ORGANOMETALLICS, vol. 23, no. 5, 2004, pages 1042 - 1054, XP002984486
DENMARK, S.E. ET AL.: "Effect of Ligand Structure in the Bisoxazoline Mediated Asymmetric Addition of Methyllithium to Imines", J.ORG.CHEM, vol. 65, no. 18, 2000, pages 5875 - 5878, XP002984487
JOURNAL OF ORGANIC CHEMISTRY, vol. 65, 2000, pages 5875
See also references of EP 1674445A4
Attorney, Agent or Firm:
Enomoto, Masayuki c/o Sumitomo Chemical Intellectual (Property Service Limited,, 5-33, Kitahama
4-chome,, Chuo-ku, Osaka-sh, Osaka 50, JP)
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