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/2005/073196
Kind Code:
A1
Abstract:
A compound of the following formula (I). This compound (I) can be produced by reacting a 1,1'-binaphthyl 2,2'-dimethylenebromide derivative which can be produced through a relatively small number of steps with an easily available secondary amine. The compound (I) is useful as a chiral phase-transfer catalyst.
Inventors:
MARUOKA KEIJI (JP)
Application Number:
PCT/JP2005/001623
Publication Date:
August 11, 2005
Filing Date:
January 27, 2005
Export Citation:
Assignee:
NAGASE & CO LTD (JP)
MARUOKA KEIJI (JP)
MARUOKA KEIJI (JP)
International Classes:
C07C227/10; C07C229/34; C07C229/36; C07C249/02; C07C251/24; C07D223/14; C07D405/14; C07D409/14; C07D471/10; C07D487/10; C07D498/10; (IPC1-7): C07D223/14; C07D498/10; C07D487/10; C07D471/10; C07D405/14; C07D409/14; C07C249/02; C07C251/24; C07C229/34; C07C227/10
Foreign References:
| JP2001048866A | 2001-02-20 |
Other References:
OOI T.: "Design of N-Spiro C2-Symmetric Chiral Quaternary Ammonium Bromidus 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.: "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
ABBOT A.P.: "Electrochemical recognition of charged species using quaternary ammonium binaphthyl salts", ANALYST, vol. 126, no. 11, 2001, CAMBRIDGE, UNITED KINGDOM, pages 1892 - 1896, XP002987954
STARA I.G.: "Nucleophilic cleavage of 4,5-dihydro-3H-dinaphth[2,1-c:1',2'-e]azepinium quaternary salts. A convenient approach to new axially dissymmetric and axially asymmetric ligands", JOURNAL OF ORGANIC CHEMISTRY, vol. 57, no. 25, 1992, pages 6966 - 6969, XP002278771
STARA I.G.: "Stereochemical Dichotomy in the Stevens Rearrangement of Axially Twisted Dihydroazepinium and Dihydrothiepinium Salts. A Novel Enantioselective Synthesis of Pentahelicene", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 116, no. 12, 1994, pages 5084 - 5088, XP002987955
STARA I.G.: "Nucleophilic Attack on 4,5-Dihydro-4-alkyl-3H-dinaphtho[2,1-c:1',2'-e]thiepinium Salts. A Convenient Approach to New 2,2'-Bidentate 1,1'-Binaphthalene Ligands with Sulfur Donor Atoms", JOURNAL OF ORGANIC CHEMISTRY, vol. 59, no. 6, 1994, pages 1326 - 1332, XP002278772
STARA I.G.: "Optically pure (S)- and (R)-4,5-dihydro-3H-4-methyldinaphth[2.1-c:1',2'-e]azepines. Application to the synthesis of new bidentate ligands with axial asymmetry", TETRAHEDRON: ASYMMETRY, vol. 33, no. 11, 1992, pages 1365 - 1368, XP002987956
COTTINEAU F.: "Reductive cleavage of axially disymmetric tertiary amines and quaternary ammonium salts by lithium aluminum hydride. Synthesis of new 1,1'-binaphthyl substituted amines", TETRAHEDRON LETTERS, vol. 26, no. 4, 1985, pages 421 - 424, XP002278770
DI BARI L.: "Conformational Study of 2,2'-Homosubstituted 1,1'-Binaphthyls by Means of UV and CD Spectroscopy", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 121, no. 35, 1999, pages 7998 - 8004, XP002987957
SHI M.: "Synthesis of axially dissymmetric chiral ammonium salts by quaternization of secondary amines (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, XP002987958
MASON S.F.: "Optical activity in the biaryl series", TETRAHEDRON, vol. 30, no. 12, 1974, pages 1671 - 1682, XP002987959
KANO T.: "Design of new polyamine-based chiral phase-transfer catalysts for the enantioselective synthesisof phenylalanine", TETRAHEDRON : ASYMMETRY, vol. 15, no. 8, 2004, pages 1243 - 1245, XP004501840
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
ABBOT A.P.: "Electrochemical recognition of charged species using quaternary ammonium binaphthyl salts", ANALYST, vol. 126, no. 11, 2001, CAMBRIDGE, UNITED KINGDOM, pages 1892 - 1896, XP002987954
STARA I.G.: "Nucleophilic cleavage of 4,5-dihydro-3H-dinaphth[2,1-c:1',2'-e]azepinium quaternary salts. A convenient approach to new axially dissymmetric and axially asymmetric ligands", JOURNAL OF ORGANIC CHEMISTRY, vol. 57, no. 25, 1992, pages 6966 - 6969, XP002278771
STARA I.G.: "Stereochemical Dichotomy in the Stevens Rearrangement of Axially Twisted Dihydroazepinium and Dihydrothiepinium Salts. A Novel Enantioselective Synthesis of Pentahelicene", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 116, no. 12, 1994, pages 5084 - 5088, XP002987955
STARA I.G.: "Nucleophilic Attack on 4,5-Dihydro-4-alkyl-3H-dinaphtho[2,1-c:1',2'-e]thiepinium Salts. A Convenient Approach to New 2,2'-Bidentate 1,1'-Binaphthalene Ligands with Sulfur Donor Atoms", JOURNAL OF ORGANIC CHEMISTRY, vol. 59, no. 6, 1994, pages 1326 - 1332, XP002278772
STARA I.G.: "Optically pure (S)- and (R)-4,5-dihydro-3H-4-methyldinaphth[2.1-c:1',2'-e]azepines. Application to the synthesis of new bidentate ligands with axial asymmetry", TETRAHEDRON: ASYMMETRY, vol. 33, no. 11, 1992, pages 1365 - 1368, XP002987956
COTTINEAU F.: "Reductive cleavage of axially disymmetric tertiary amines and quaternary ammonium salts by lithium aluminum hydride. Synthesis of new 1,1'-binaphthyl substituted amines", TETRAHEDRON LETTERS, vol. 26, no. 4, 1985, pages 421 - 424, XP002278770
DI BARI L.: "Conformational Study of 2,2'-Homosubstituted 1,1'-Binaphthyls by Means of UV and CD Spectroscopy", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 121, no. 35, 1999, pages 7998 - 8004, XP002987957
SHI M.: "Synthesis of axially dissymmetric chiral ammonium salts by quaternization of secondary amines (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, XP002987958
MASON S.F.: "Optical activity in the biaryl series", TETRAHEDRON, vol. 30, no. 12, 1974, pages 1671 - 1682, XP002987959
KANO T.: "Design of new polyamine-based chiral phase-transfer catalysts for the enantioselective synthesisof phenylalanine", TETRAHEDRON : ASYMMETRY, vol. 15, no. 8, 2004, pages 1243 - 1245, XP004501840
Attorney, Agent or Firm:
Nanjo, Hiromichi (Okina Bldg. 2-9, Nishitenma 3-chome, Kita-k, Osaka-shi Osaka, JP)
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