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Title:
GUANIDINE COMPOUND AND ASYMMETRIC REACTION USING THE SAME
Document Type and Number:
WIPO Patent Application WO/2005/077908
Kind Code:
A1
Abstract:
A guanidine compound which has a bi-aryl skeleton represented by the following general formula (1): [wherein R1, R2 and R3 each independently represents a hydrogen atom, a hydrocarbon group optionally having a substituent or a heterocyclic group optionally having a substituent, R4 to R15 each independently represents a hydrogen atom, a hydrocarbon group optionally having a substituent, a heterocyclic group optionally having a substituent, a hydroxyl group, an alkoxy group optionally having a substituent, an aryloxy group optionally having a substituent, an acyl group, an alkoxycarbonyl group optionally having a substituent, an aryloxycarbonyl group optionally having a substituent, a carbamoyl group optionally having a substituent, an alkylthiocarbonyl group optionally having a substituent, an arylthiocarbonyl group optionally having a substituent, a carboxyl group, an alkylthio group optionally having a substituent, an arylthio group optionally having a substituent, an amino group or a substututed amino group, or a substituted silyl group, and in any combination of R1 to R15, these substituents may together bind with each other to form a ring, and X1 to X8 each represents a carbon atom or a nitrogen atom, with the proviso that each of X1 to X8 has no substituent when it is nitrogen]. The above guanidine compound is useful as a catalyst for a variety of asymmetric reactions.

Inventors:
TERADA MASAHIRO (JP)
UBE HITOSHI (JP)
YOKOYAMA SHIGEKO (JP)
SHIMIZU HIDEO (JP)
Application Number:
PCT/JP2005/001943
Publication Date:
August 25, 2005
Filing Date:
February 09, 2005
Export Citation:
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Assignee:
TAKASAGO PERFUMERY CO LTD (JP)
TERADA MASAHIRO (JP)
UBE HITOSHI (JP)
YOKOYAMA SHIGEKO (JP)
SHIMIZU HIDEO (JP)
International Classes:
C07B53/00; C07B61/00; C07C201/12; C07C205/16; C07C205/40; C07D223/28; C07D245/04; C07D301/12; C07D301/14; C07D301/16; C07D301/19; C07D303/32; (IPC1-7): C07D223/28; C07D301/12; C07D301/14; C07D301/19; C07D303/32; C07B61/00; C07C201/12; C07C205/40; C07C205/16; C07M7/00
Foreign References:
JP2000198774A2000-07-18
JP2001048866A2001-02-20
JPS61161266A1986-07-21
Other References:
ABOUL-ENEIN H.Y. ET AL: "Synthesis and biological activity of dibenz[c,elazepines", DRUG DESIGN AND DELIVERY, vol. 4, no. 1, 1988, pages 27 - 33, XP002987985
CHINCHILLA R. ET AL: "Enantiomerically pure guanidine-catalysed asymmetric nitroaldol reaction", TETRAHEDRON: ASYMMETRY, vol. 5, no. 7, 1994, pages 1393 - 1402, XP002332063
ALLINGHAM M.T. ET AL: "Synthesis and applications of C2-symmetric quanidine bases", TETRAHEDRON LETTERS, vol. 44, no. 48, 2003, pages 8677 - 8686, XP004468500
OOI T. ET AL: "Design of N-spiro C2-symmetric chiral quaternary ammonium bromides as novel chiral phase-transfer catalysts: synthesis and application to practical asymmetric synthesis of alpha-amino acids", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 125, no. 17, 2003, pages 5139 - 5151, XP002331142
OOI T. ET AL: "Practical Catalytic Enantioselective Synthesis of alpha,alpha-Dialkyl-alpha-Amino Acids by Chiral Phase-Transfer Catalysis", J AM CHEM SOC, vol. 122, no. 21, 2000, pages 5228 - 5229, XP002941729
OOI T. ET AL: "Molecular Design of a C2-Symmetric Chiral Phase Transfer Catalyst for Practical Asymmetric Synthesis of alpha-Amino Acids", J AM CHEM SOC, vol. 121, no. 27, 1999, pages 6519 - 6520, XP002941730
Attorney, Agent or Firm:
Iwatani, Ryo (1-31 Dojima 2-chome, Kita-k, Osaka-shi Osaka, JP)
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