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)
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:
Assignee:
TAKASAGO PERFUMERY CO LTD (JP)
TERADA MASAHIRO (JP)
UBE HITOSHI (JP)
YOKOYAMA SHIGEKO (JP)
SHIMIZU HIDEO (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:
JP2000198774A | 2000-07-18 | |||
JP2001048866A | 2001-02-20 | |||
JPS61161266A | 1986-07-21 |
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
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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