Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2007-12-25
2007-12-25
Seaman, Margaret D. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C546S134000, C546S136000
Reexamination Certificate
active
11140574
ABSTRACT:
One aspect of the present invention relates to quinine-based and quinidine-based catalysts. Another aspect of the invention relates to a method of preparing a derivatized quinine-based or quinidine-based catalyst comprising 1) reacting quinine or quinidine with base and a compound that has a suitable leaving group, and 2) converting the ring methoxy group to a hydroxy group. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral ketone, comprising the step of: reacting a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral ketone with a nucleophile in the presence of a catalyst; thereby producing a chiral, non-racemic compound; wherein said catalyst is a derivatized quinine or quinidine. Another aspect of the present invention relates to a method of kinetic resolution, comprising the step of: reacting racemic chiral alkene with a nucleophile in the presence of a derivatized quinine or quinidine.
REFERENCES:
patent: WO 02/05953 (2002-01-01), None
patent: WO 03/011799 (2003-02-01), None
Suzko et al., Roczniki Chemii, 1925, “B-Isoquinine and niquine”, vol. 5, pp. 358-385.
Barnes, D. M. et al., “Development of a Catalytic Enantioselective Conjugate Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes for the Synthesis of Endothelin-A Antagonist ABT-546. Scope, Mechanism, and Further Application to the Synthesis of the Antidepressant Rolipram”,J. Am. Chem. Soc., 124:13097-13105 (2002).
Berner, O. M. et al., “Asymmetric Michael Additions to Nitroalkenes”,Eur. J. Org. Chem., 1877-1894 (2002).
Brunner, H. et al., “Asymmetric Catalysis, CIII[1]: EnantioselectiveMichaelAddition of 1,3-Dicarbonyl Compounds to Conjugated Nitroalkenes”,Monatshefte für Chemie, 127:1063-1072 (1996).
Calter, M. A., “Catalytic, Asymmetric Dimerization of Methylketene”,J. Org. Chem., 61:8006-8007 (1996).
Chen, Y, et al., “Asymmetric Alcoholysis of Cyclic Anhydrides”,Chem. Rev., 103:2965-2983 (2003).
Cortez. G. S. et al., “Bicyclic β-Lactones via Intramolecular NCAL Reactions with Cinchona Alkaloids: Effect of the C9-Substituent on Enantioselectivity and Catalyst Conformation”,Synthesis, 11:1731-1736 (2001).
Cortez. G. S. et al., “Intramolecular, Nucleophile-Catalyzed Aldol-Lactonization (NCAL) Reactions: Catalytic, Asymmetric Synthesis of Bicyclic β-Lactones”,J. Am. Chem. Soc., 123:7945-7946 (2001).
France, S. et al., “Nucleophilic Chiral Amines as Catalysts in Asymmetric Synthesis”,Chem. Rev., 103:2985-3012 (2003).
Gröger, H., “The Development of New Monometallic Bifunctional Catalysts with Lewis acidandLewis Base Properties, and their Application in Asymmetric Cyanation Reactions”,Chem. Eur. J., 7(24):5247-5251 (2001).
Hiemstra, H. et al., “Addition of Aromatic Thiols to Conjugated Cycloalkenones, Catalyzed by Chiral β-Hydroxy Amines. A Mechanistic Study on Homogeneous Catalytic Asymmetric Synthesis”,J. Am. Chem. Soc., 103:417-430 (1981).
Iwabuchi, Y. et al., “Chiral Amine-Catalyzed Asymmetric Baylis-Hillman Reaction: A Reliable Route to Highly Enantiomerically Enriched (α-Methylene-β-hydroxy)esters”,J. Am. Chem. Soc., 121:10219-10220 (1999).
Ji, J. et al., “Catalytic Enantioselective Conjugate Additin of 1,3-Dicarbonyl Compounds to Nitroalkenes”,J. Am. Chem. Soc., 121:10215-10216 (1999).
Kawahara, S. et al., “β-Isocupreidine-Catalyzed Asymmetric Baylis-Hillman Reaction of Imines”,Organic Letters, 5(17):3103-3105 (2003).
List, B., “Asymmetric Aminocatalysis”,Synlett, 11:1675-1686 (2001).
List, B., “Proline-catalyzed asymmetric reactions”,Tetrahedron, 58:5573-5590 (2002).
Marcelli, T. et al., “Cinchona Derivatives as Bifunctional Organocatalysts for the Direct Asymmetric Nitroaldol (Henry) Reaction”,Synlett., 18:2817-2819 (2005).
Okino, T. et al., “EnantioselectiveMichaelReaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts”,J. Am. Chem. Soc., 125:12672-12673 (2003).
Rogers. L. M.-A. et al., “Enantioselective decarboxylation-reprotonation of an α-amino malonate derivative as a route to optically enriched cyclic α-amino acid”,Tetrahedron Letters, 44:3047-3050 (2003).
Shibasaki, M. et al., “Asymmetric Catalysis with Heterobimetallic Compounds”,Angew. Chem. Int. Ed. Engl., 36:1236-1256 (1997).
Shibasaki, M. et al., “Lanthanide Complexes in Multifunctional Asymmetric Catalysis”,Chem. Rev., 102:2187-2209 (2002).
Sibi, M. P. et al., “Enantioselective Conjugate Additions”,Tetrahedron, 56:8033-8061 (2000).
Taggi, A. E. et al., “Catalytic, Asymmetric Synthesis of β-Lactams”,J. Am. Chem. Soc., 122:7831-7832 (2000).
Tian, S-K, et al., “Asymmetric Organic Catalysis with Modified Cinchona Alkaloids”,Acc. Chem. Res. (abstract), Dec. 10, 2003.
Wack, H. et al., “Catalytic, Asymmetric α-Halogenation”,J. Am. Chem. Soc., 123:1531-1532 (2001).
Wynberg, H.,Asymmetric Catalysis by Alkaloids, Department of Chemistry, University of Groningen, The Netherlands, 88-127.
Heimstra, H. et al., “Addition of Aromatic Thiols to Conjugated Cycloalkenones, Catalyzed by Chiral β-Hydroxy Amines. A Mechanistic Study on Homogeneous Catalytic Asymmetric Syntehesis”,J. Am. Chem. Soc., 103:417-430 (1981).
Li, H. et al., “Catalytic Enantioselective C-C Bond Forming Conjugate Additional with Vinyl Sulfones”,J. Am. Chem. Soc., 127:8948-8949 (2005).
Li, H. et al., “Highly Enantioselective Conjugate Addition of Malonate and β-Ketoester to Nitroalkenes: Asymmetric C-C Bond Formation with New Bifunctional Organic Catalysts Based on Cinchona Alkaloids”,J. Am. Chem. Soc., 126:9906-9907 (2004).
Li, H. et al., “Stereocontrolled Creation of Adjacent Quaternary and Tertiary Stereocenters by a Catalytic Conjugate Addition”,Angew. Chem. Int. Ed., 44:105-108 (2005).
Liu, X. et al., “Highly Enantioselective Amination of α-Substituted α-Cyanoacetates with Chiral Catalysts Accessible from Both Quinine and Quinidine”,Organic Letters, 7(2):167-169 (2005).
Rogers, L. M. A. et al., “Enantioselective decarboxylation-reprotonation of an α-amino malonate derivative as a route to optically enriched cyclic α-amino acid”,Tetrahedron Letters, 44:3047-3050 (2003).
Wynberg, H., “Asymmetric Catalysts by Alkaloids”,Top. Stereochem., 16:87-129 (1986).
Deng Li
Li Hongming
Brandeis University
Foley & Hoag LLP
Gordon Dana M.
Rahmani Niloofar
Seaman Margaret D.
LandOfFree
Asymmetric Michael and Aldol additions using bifunctional... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Asymmetric Michael and Aldol additions using bifunctional..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Asymmetric Michael and Aldol additions using bifunctional... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3898367