Title:
OPTICALLY ACTIVE QUATERNARY AMMONIUM SALT HAVING AXIAL ASYMMETRY AND PROCESS FOR PRODUCING &agr -AMINO ACID AND DERIVATIVE THEREOF WITH THE SAME
Document Type and Number:
WIPO Patent Application WO/2006/104226
Kind Code:
A1
Abstract:
A chiral phase-transfer catalyst represented by the following formula (I). (I) The compound (I) can be produced by reacting 1,1'-biphenyl 2,2'-dimethylenebromide derivative which can be produced through a relatively small number of steps with an easily available secondary amine.
Inventors:
MARUOKA KEIJI (JP)
NISHIMOTO YUKIFUMI (JP)
YAMAMOTO KENICHIRO (JP)
NISHIMOTO YUKIFUMI (JP)
YAMAMOTO KENICHIRO (JP)
Application Number:
PCT/JP2006/306791
Publication Date:
October 05, 2006
Filing Date:
March 24, 2006
Export Citation:
Assignee:
NAGASE & CO LTD (JP)
UNIV KYOTO (JP)
MARUOKA KEIJI (JP)
NISHIMOTO YUKIFUMI (JP)
YAMAMOTO KENICHIRO (JP)
UNIV KYOTO (JP)
MARUOKA KEIJI (JP)
NISHIMOTO YUKIFUMI (JP)
YAMAMOTO KENICHIRO (JP)
International Classes:
C07D223/18; B01J31/02; C07C227/04; C07C227/32; C07C229/36; C07C249/02; C07C251/24; C07D487/10; C07D498/10; C07D513/10; C07B53/00; C07B61/00
Foreign References:
| JP2004359578A | 2004-12-24 | |||
| JP2002326992A | 2002-11-15 | |||
| JP2001048866A | 2001-02-20 | |||
| JP2003081976A | 2003-03-19 | |||
| JP2004359578A | 2004-12-24 | |||
| JP2002326992A | 2002-11-15 | |||
| EP1854796A1 | 2007-11-14 |
Other References:
OOI T.: "A new N-spiro C2-symmetric chiral quaternary ammonium bromide consisting of 4,6-disubstituted biphenyl subunit as an efficient chiral phase-transfer catalyst", SYNLETT, no. 12, 2003, pages 1931 - 1933, XP008122016
KASHIWADA Y.: "New hexahydroxybiphenyl derivatives as inhibitors of protein kinase C", JOURNAL OF MEDICINAL CHEMISTRY, vol. 37, no. 1, 1994, pages 195 - 200, XP000570406
INSOLE J.M.: "Steric effects of methoxy groups in 2,2'-bridged biphenys.II", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 2: PHYSICAL ORGANIC CHEMISTRY, no. 9, 1972 - 1999, pages 1168 - 1173, XP003021755
DATABASE CA [online] BEAVEN G.H.: "Relation between configuration and conjugation in diphenyl derivatives.I. The enantionorphism and ultraviolet absorption spectra of some 2,2'bridged compounds", XP008115897, Database accession no. (46:67079)
DATABASE CA [online] FITTS D.D.: "Configurational studies in the biphenyl series.IV.Conformation and optical rotation of restricted biphenyls. Configuration correlation of biaryls by optical displacement. The absolute configuration of restricted 1,1'-binaphthyls", XP008115896, Database accession no. (52:55790)
DATABASE AC [online] AHMED, SHAKTI R.: "Steric effects in 2,2'-bridged biphenyls with a heterocyclic bridging ring.I. Optically active dihydrodibenzazepines", XP008115895, Database accession no. (53:2119)
DATABASE CA [online] AHMED, SHAKTI R.: "Steric effects in 2,2'-bridged biphenyls with a heterocyclic bridging ring.III. Ultraviolet absorption spectra of some dihydrodibenzazepinium compounds", XP008115893, Database accession no. (55:38083)
LYGO B.: "Identification of a highly effective asymmetric phase-transfer catalyst derived from a-methylnapthylamine", TETRAHEDRON LETTERS, vol. 44, no. 30, 2003, pages 5629 - 5632, XP004433813
SHI M.: "Synthesis of axially dissymmetric chiral ammonium salts by quaternization of secondary amines with (R) - (+) -2,2'-bis(bromomethyl)-6,6'-dinitrobiphenyl and (R) - (+) -2,2'bis(bromomethyl)-1,1'binaphthyl and an examination of their abilities as chiral phase-transfer catalysts", JOURNAL OF CHEMICAL RESEARCH, SYNOPSES, no. 2, 1995, pages 46 - 47, XP008122082
OOI T.: "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
HAN, ZHENFU: "Convenient preparation of highly active phase-transfer catalyst for catalytic asymmetric synthesis of a-alkyl- and a, a-dialkyl-a-amino acids: application to the short asymmetric synthesis of BIRT-377", TETRAHEDRON LETTERS, vol. 46, no. 49, 2005, pages 8555 - 8558, XP025385472
OOI, T. ET AL., J. AM. CHEM. SOC., vol. 122, 2000, pages 5228
SYNLETT, 2003, pages 1931 - 1933
TETRAHEDRON LETTERS, vol. 44, 2003, pages 5629 - 5632
TETRAHEDRON LETTERS, vol. 46, 2005, pages 8555 - 8558
0. T. SCHMIDT; K. DEMMLER; JUSTUS LIEBIGS, ANN. CHEM., vol. 576, 1952, pages 85
See also references of EP 1870403A4
KASHIWADA Y.: "New hexahydroxybiphenyl derivatives as inhibitors of protein kinase C", JOURNAL OF MEDICINAL CHEMISTRY, vol. 37, no. 1, 1994, pages 195 - 200, XP000570406
INSOLE J.M.: "Steric effects of methoxy groups in 2,2'-bridged biphenys.II", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 2: PHYSICAL ORGANIC CHEMISTRY, no. 9, 1972 - 1999, pages 1168 - 1173, XP003021755
DATABASE CA [online] BEAVEN G.H.: "Relation between configuration and conjugation in diphenyl derivatives.I. The enantionorphism and ultraviolet absorption spectra of some 2,2'bridged compounds", XP008115897, Database accession no. (46:67079)
DATABASE CA [online] FITTS D.D.: "Configurational studies in the biphenyl series.IV.Conformation and optical rotation of restricted biphenyls. Configuration correlation of biaryls by optical displacement. The absolute configuration of restricted 1,1'-binaphthyls", XP008115896, Database accession no. (52:55790)
DATABASE AC [online] AHMED, SHAKTI R.: "Steric effects in 2,2'-bridged biphenyls with a heterocyclic bridging ring.I. Optically active dihydrodibenzazepines", XP008115895, Database accession no. (53:2119)
DATABASE CA [online] AHMED, SHAKTI R.: "Steric effects in 2,2'-bridged biphenyls with a heterocyclic bridging ring.III. Ultraviolet absorption spectra of some dihydrodibenzazepinium compounds", XP008115893, Database accession no. (55:38083)
LYGO B.: "Identification of a highly effective asymmetric phase-transfer catalyst derived from a-methylnapthylamine", TETRAHEDRON LETTERS, vol. 44, no. 30, 2003, pages 5629 - 5632, XP004433813
SHI M.: "Synthesis of axially dissymmetric chiral ammonium salts by quaternization of secondary amines with (R) - (+) -2,2'-bis(bromomethyl)-6,6'-dinitrobiphenyl and (R) - (+) -2,2'bis(bromomethyl)-1,1'binaphthyl and an examination of their abilities as chiral phase-transfer catalysts", JOURNAL OF CHEMICAL RESEARCH, SYNOPSES, no. 2, 1995, pages 46 - 47, XP008122082
OOI T.: "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
HAN, ZHENFU: "Convenient preparation of highly active phase-transfer catalyst for catalytic asymmetric synthesis of a-alkyl- and a, a-dialkyl-a-amino acids: application to the short asymmetric synthesis of BIRT-377", TETRAHEDRON LETTERS, vol. 46, no. 49, 2005, pages 8555 - 8558, XP025385472
OOI, T. ET AL., J. AM. CHEM. SOC., vol. 122, 2000, pages 5228
SYNLETT, 2003, pages 1931 - 1933
TETRAHEDRON LETTERS, vol. 44, 2003, pages 5629 - 5632
TETRAHEDRON LETTERS, vol. 46, 2005, pages 8555 - 8558
0. T. SCHMIDT; K. DEMMLER; JUSTUS LIEBIGS, ANN. CHEM., vol. 576, 1952, pages 85
See also references of EP 1870403A4
Attorney, Agent or Firm:
Nanjo, Hiromichi (Okina Bldg. 2-9, Nishitenma 3-chome, Kita-k, Osaka-shi Osaka 47, JP)
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