Optically active quaternary ammonium salt having axial...

Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C540S576000

Reexamination Certificate

active

07928224

ABSTRACT:
The present invention provides a compound of the following formula (I) below. This compound (I) can be produced by reacting a 2,2′-dimethylene bromide-1,1′-binaphthyl derivative, which can be produced by a relatively small number of processes, with an easily available secondary amine. This compound (I) is useful as a chiral phase-transfer catalyst.

REFERENCES:
patent: 6340753 (2002-01-01), Maruoka
patent: 2006/0183896 (2006-08-01), Maruoka
patent: 2007/0135654 (2007-06-01), Maruoka
patent: 2009/0054679 (2009-02-01), Maruoka et al.
patent: 2009/0270614 (2009-10-01), Maruoka et al.
patent: 2010/0029935 (2010-02-01), Maruoka et al.
patent: 1 854 796 (2007-11-01), None
patent: 1870403 (2007-12-01), None
patent: 2001-48866 (2001-02-01), None
patent: 2002-173492 (2002-06-01), None
patent: 2002-326992 (2002-11-01), None
patent: 2003-081976 (2003-03-01), None
patent: 2004-189696 (2004-07-01), None
patent: 2004-238362 (2004-08-01), None
patent: 2004-359578 (2004-12-01), None
patent: 2005-41791 (2005-02-01), None
patent: 2006054366 (2006-05-01), None
patent: 2006/093269 (2006-09-01), None
patent: 2006/104226 (2006-10-01), None
Keiji Maruoka, TCI Mail, Jul. 2001, No. 111. pp. 2-19.
European Search Report corresponding to U.S. Appl. No. 10/587,467 mailed on Jul. 8, 2009.
Abbott, et al. Electrochemical recognition of analytes using quaternary ammonium binaphthyl salts. XP002532001. 2003.
Fitts, et al. Configurational studies in the biphenyls. Configurational correlation of biaryls by optical displacement. The absolute configuration of restricted 1,1′-binaphthyls. XP002532002. 1958.
XP002532004. 1955.
XP002532005. 2006.
Bellier, et al., Synthesis and Biological Properties of New Constrained CCK-B Antagonists: Discrimination of Two Affinity States of the CCK-B Receptor on Transfected CHO Cells, J. Med. Chem., vol. 40, No. 24, pp. 3947-3956, 1997.
Shioiri, et al., Asymmetric Phase Transfer Catalysis, Stimulating Concepts in Chemistry, pp. 123-143, 2000, Wiley-VCH, Weinheim.
Ooi, et al., Practical Catalytic Enantioselective Synthesis of a,a-Dialkyl-a-Amino Acids by Chiral Phase-Transfer Catalysis, J. Am. Chem. Soc., vol. 122, pp. 5228-5229, 2000.
Seki, et al., A Practical Synthesis of C2-Symmetric Chiral Binaphthyl Ketone Catalyst, Synthesis, No. 12, pp. 1677-1680, 2000.
Ooi, et al., New, Improved Procedure for the Synthesis of Structurally Diverse N-Spiro C2-Symmetric Chiral Quaternary Ammonium Bromides, J. Org. Chem., vol. 68, pp. 4576-4578, 2003.
Ooi, 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 a-Amino Acids, J. Am. Chem. Soc., vol. 125, No. 17, pp. 5139-5151, 2003.
Ooi, et al., Molecular Design of a C2-Symmetric Chiral Phase-Transfer Catalyst for Practical Asymmetric Synthesis of a-Amino Acids, J. Am. Chem. Soc., vol. 121, No. 27, pp. 6519-6520, 1999.
Stara, et al., 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, J. Org. Chem., vol. 57, No. 25, pp. 6966-6969, 1992.
Di Bari, et al., Conformational Study of 2,2′-Homosubstituted 1,1′-Binaphthyls by Means of UV and CD Spectroscopy, J. Am. Chem. Soc., vol. 121, No. 35, pp. 7998-8004, 1999.
Shi, et al., 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, pp. 46-47, 1995.
Kano, et al., Design of New Polyamine-based Chiral Phase-Transfer Catalysts for the Enantioselective Synthesis of Phenylalanine, Tetrahedron: Asymmetry, vol. 15, No. 8, pp. 1243-1245, 2004.
Ikunaka, et al., A Scalable Synthesis of (R)-3,5-Dihydro-4H-dinaphth[2,1-c:1′2′-e]azepine, Organic Process Research & Development, vol. 7, No. 5, pp. 644-648, 2003.
Mossel, et al., Aspartame Dipeptide Analogues: Effect of Number of Side-Chain Methylene Group Spacers and C-Methylation in the Second Position, Tetrahedron Asymmetry, vol. 8, pp. 1305-1314, 1997.
O'Donnell, The Preparation of Optically Active a-Amino Acids From the Benzophenone Imines of Glycine Derivatives, M. J. Aldrichimica Acta, vol. 34, No. 1, pp. 3-15, 2001.
Abbott, et al., Electrochemical Recognition of Charged Species Using Quaternary Ammonium Binaphthyl Salts, A. P., Analyst, vol. 126, No. 11, pp. 1892-1896, 2001 UK.
Stara, et al., Stereochemical Dichotomy in the Stevens Rearrangement of Axially Twisted Dihydroazepinium and Dihydrothiepinium Salts. A Novel Enantioselective Synthesis of Pentahelicene, J. Am. Chem. Soc., vol. 116, No. 12, pp. 5084-5088, 1994.
Stara, et al., 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, J. Org. Chem., vol. 59, No. 6, pp. 1326-1332, 1994.
Stara, et al., 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. 3, No. 11, pp. 1365-1368, 1992, Great Britian.
Cottineau, et al., Reductive Cleavage of Axially Dismmetric Tertiary Amines and Quaternary Ammonium Salts by Lithium Aluminium Hydride. Synthesis of New 1,1′-Binaphthyl Substituted Amines, Tetrahedron Letters, vol. 26, No. 4, pp. 421-424, 1985, Great Britian.
Mason, et al., Optical Activity in the Biaryl Series, Tetrahedron, vol. 30, No. 12, pp. 1671-1682, 1974, Great Britian.
Kitamura, et al., Powerful Chiral Phase-Transfer Catalysts for the Asymmetric Synthesis of a-Alkyl-and a,a-Dialkyl-a-amino Acids, Angew. Chem. Int. Ed., vol. 44, pp. 1549-1551, 2005.
International Search Report for PCT/JP2005/001623, Dated Mar. 22, 2005.
International Preliminary Examination Report for PCT/JP2005/001623, Dec. 7, 2005.
U.S. Office Action dated May 3, 2010 corresponding to U.S. Appl. No. 11/626,228, filed Jan. 23, 2007.
Ahmed et al., Chemical Abstract 53:2119, OREF 53: 405c-i, 406a, Journal of the Chemical Society, p. 3043-3047, 1958.
Ahmed et al., Chemical Abstract 55:38083, OREF 55: 7430c-f, Journal of the Chemical Society, p. 4165-4169, 1960.
Beaven et al., Chemical Abstract 46:67079, OREF 46: 11211e-i, 11212a-I, Journal of the Chemical Society, vol. 46, p. 854-868, 1952.
Han et al., Tetrahedron Letters, vol. 46, No. 49, p. 8555-8558, 2005.
Insole, Journal of the Chemical Society. Perkin transactions 2: physical organic chemistry, No. 9, p. 1168-1173, 1972.
Kashiwada et al., Journal of Medical Chemistry, vol. 37, No. 1, p. 195-200, 1994.
Lygo et al., Tetrahedron Letters, vol. 44, No. 30, p. 5629-5632, 2003.
Ooi et al., Synlett., No. 12, p. 1931-1933, 2003.
Reitz et al., Holzforschung, vol. 55, No. 2, p. 171-175, 2001.
Schmidt et al., Ann. Chem., vol. 576, p. 85-93, 1952.
Costero et al., Anales de Quimica, vol. 89, No. 1, p. 95-98, 1993.
Wang et al., Tetrahedron, vol. 63, No. 26, p. 6042-6050, 2007.
Wang et al., Organic Process Research & Development, vol. 11, No. 3, p. 628-632, 2007.
Arimura et al., The Chemical Society of Japan, Dai 86 Shunki Nenkai (2006), Koen Yokoshu II, p. 1073, Mar. 13, 2006.
Belokon et al., Tetrahedron, vol. 60, No. 8, p. 1849-1861, 2004.
Chen et al., Youji Huaxue, vol. 8, No. 2, p. 164-166, 1988.
Maruoka et al., Chemical Reviews, vol. 103, No. 8, p. 3013-3028, 2003.
Bey et al., Tetrahedron Letter, vol. 18, No. 17, p. 1455-1458, 1977.
O'Donnell et al., J. Am. Chem. Soc., vol. 111, p. 2353-2355, 1989.
Park et al., J. Org. Chem. vol. 70, p. 1904-1906, 2005.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Optically active quaternary ammonium salt having axial... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Optically active quaternary ammonium salt having axial..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Optically active quaternary ammonium salt having axial... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2641457

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.