Optically active β-aminoketones, optically active...

Details Optically active β-aminoketones, optically active... Optically active β-aminoketones, optically active...

2007-01-09

2007-01-09

Mckenzie, Thomas (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C564S305000

Reexamination Certificate

active

10430023

ABSTRACT:
The invention relates to chiral Mannich bases of formula (I), chiral 1,3-amino alcohols of formula (II) derived therefrom, wherein R1, R2, R3, R4and R5are as defined herein, and to processes for preparing Mannich salts of formula (III) containing a chiral anion Y*−and compounds of formulae (I) and (II), wherein R1, R2, R3, R4, R5and Y*−are as defined herein.

REFERENCES:
patent: 5916786 (1999-06-01), Rozzell, Jr.
patent: 6180618 (2001-01-01), Stengelin et al.
patent: 6245744 (2001-06-01), Frick
patent: 6303639 (2001-10-01), Frick et al.
patent: 6566340 (2003-05-01), Frick
patent: 6569835 (2003-05-01), Frick
patent: 6596728 (2003-07-01), Kirsch et al.
patent: WO 98/42643 (1998-10-01), None
“Three-component carbon—carbon bond-forming reactions catalyzed by a Bronsted acid-surfactant -combined catalyst in water”, Manable et. al., Tetrahedron 57 (2001)2537-2544.
Akiyama, et al., HBF4 Catalyzed Mannich-Type Reaction in Aqueous Media, Synlett; 1999; No. 07; pp. 1045-1048.
Andrisano, et al., Stereochemistry of Mannich Bases—V: Lithium Aluminium Hydride Reduction of alpha-Asymmetric-beta-Amino Propiophenones and relative Configuration of the Corresponding Amino-Alcohols, Tetrahedron; 1970; 26; pp. 5247-5253.
Arend, et al., Modern Variants of the Mannich Reaction, Angew. Chem. Int. Ed.Engl.; 1998; 37; pp. 1045-1070.
Barluenga, et al., Diastereoselective Synthesis of gamma-Amino Alcohols with Three Chiral Centers by Reduction of beta-Amino Ketones and Derivatives, J. Org. Chem.; 1985; 50; pp. 4052-4056.
Brienne, et al., Reduction par I′hyrure de lithium et d′aluminium de beta-aminocetones, Bulletin de la Societe Chimique de France; 1969; 7; pp. 2395-2407.
Cicchi, et al., Synthesis of New Enantiopure gamma-aminoalcohols: their use as catalysts in the Alkylation of Benzaldehyde by Diethylzinc, Tetrahedron: Asymmetry; 1997; 8; 2; pp. 293-301.
Couturier, et al., Palladium Catalyzed Activation of Borane-amine Adducts: Rate Enhancement of Amine-borane Methanolysis in the Reduction of Nitrobenzenes to Anilines, Tetrahedron Letters; 2001; 42; pp. 2285-2288.
Denmark, et al., Catalytic Enantioselective Mannich-Type Reactions, Comprehensive Asymmetric Catalysis; Springer-Verlag:New York; 1999, vol. 2; Chapter 26.2.9; pp. 954-958.
Groger, et al., The Application of L-Proline as an Enzyme Mimic and Further New Asymmetric Using Small Organic Molecules as Chiral Catalysts, Agnew. Chem. Int. Ed.; 2001; 40; 3; pp. 529-532.
Ishitani, et al., Enantioselective Mannich-Type Reactions Using a Novel Chiral Zirconium Catalyst for the Synthesis of Optically Active beta-Amino Acid Derivatives, J. Am. Chem Soc.; 2000; 122, pp. 8180-8186.
Jiang, et al., Highly Enantioselective Reduction of Achiral Ketones with NaBH4/Me3SiCl Catalyzed by (S)-alpha,alpha-diphenylpyrrolidinemethanol, tetrahedron Letters; 2000; 41; pp. 10281-10283.
List, Benjamin, The Direct Catalytic Asymmetric Three-Component Mannich Reaction, J. AM. Chem. Soc.; 2000; 122; pp. 9336-9337.
Nolen, et al., Diastereoselectivity in the Synthesis of Mannich Bases, Tetrahedron Letters; 1991; 32; 1; pp. 73-74.
Shida, et al., Nickel Catalyzed Imine Aldol Reactions between Activated Imines and Pronucleophiles, Tetrahedron Letters; 1995; 36; 28; pp. 5023-5026.
Yamasaki, et al., Direct catlylic Asymmetric Mannich-type Reaction of Unmodified Ketones utilizing the Cooperation of an AlLibis(binaphthoxide Complex and La(OTf)3.nH2O, Tetrahedron Letters; 40; 1999; pp. 307-310.
Akiyama, et al., HBF4 Catalyzed Mannich-Type Reaction in Aqueous Media, Synlett; 1999; No. 07; pp. 1045-1048.
Andrisano, et al., Stereochemistry of Mannich Bases—V: Lithium Aluminum Hydride Reduction of alpha-Asymmetric-beta-Amino Propiophenones and relative Configuration of the Corresponding Amino-Alcohols, Tetrahedron; 1970; 26; pp. 5247-5253.
Arend, et al., Modern Variants of the Mannich Reaction, Angew. Chem. Int. Ed.Engl.; 1998; 37; pp. 1045-1070.
Barluenga, et al., Diastereoselective Synthesis of gamma-Amino Alcohols with Three Chiral Centers by Reduction of beta-Amino Ketones and Derivatives, J. Org. Chem.; 1985; 50; pp. 4052-4056.
Brienne, et al., Reduction par I′hyrure de lithium el d′aluminium de beta-aminocetones, Bulletin de la Societe Chimique de France; 1969; 7: pp. 2395-2407.
Cicchi, et al., Synthesis of New Enantiopure gamma-aminoalcohols: their use as catalysts in the Alkylation of Benzaldehyde by Diethylzinc, Tetrahedron: Asymmetry; 1997; 8; 2; pp. 293-301.
Couturier, et al., Palladium Catalyzed Activation of Borane-amine Adducts: Rate Enhancement of Amine-borane Methanolysis in the Reduction of Nitrobenzenes to Anilines, Tetrahedron Letters; 2001; 42; pp. 2285-2288.
Denmark, et al., Catalytic Enantioselective Mannich-Type Reactions, Comprehensive Asymmetric Catalysis; Springer-Verlag:New York; 1999, vol. 2; Chapter 26.2.9; pp. 954-958.
Groger, et al., The Application of L-Proline as an Enzyme Mimic and Further New Asymmetric Using Small Organic Molecules as Chiral Catalysts, Agnew. Chem. Int. Ed.;2001; 40; 3; pp. 529-532.
Ishitani, et al., Enantioselective Mannich-Type Reactions Using a Novel Chiral Zirconium Catalyst for the Synthesis of Optically Active beta-Amino Acid Derivatives, J. Am. Chem Soc.; 2000; 122, pp. 8180-8186.
Jiang, et al., Highly Enantioselective Reduction of Achiral Ketones with NaBH4/Me3SiCl Catalyzed by(S)-alpha, alpha-diphenylpyrrolidinemethanol, tetrahedron Letters; 2000; 41; pp. 10281-10283.
List, Benjamin, The Direct Catalytic Asymmetric Three-Component Mannich Reaction, J. AM. Chem. Soc.; 2000; 122; pp. 9336-9337.
Nolen, et al., Diastereoselectivity in the Synthesis of Mannich Bases, Tetrahedron Letters; 1991; 32; 1; pp. 73-74.
Shida, et al., Nickel Catalyzed Imine Aldol Reactions between Activated Imines and Pronucleophiles, Tetrahedron Letters; 1995; 36; 28; pp. 5023-5026.
Yamasaki, et al., Direct catlytic Asymmetric Mannich-type Reaction of Unmodified Ketones utilizing the Cooperation of an AlLibis(binaphthoxide Complex and La(OTf)3.nH2O, Tetrahedron Letters; 40; 1999; pp. 307-310.
Akiyama, et al, HBF4 Catalyzed Mannich-Type Reaction in Aqueous Media, Synlett; 1999; No. 07; pp. 1045-1048.
Andrisano, et al., Stereochemistry of Mannich Bases—V: Lithium Aluminum Hydride Reduction of alpha-Asymmetric-beta-Amino Propiophenones and relative Configuration of the Corresponding Amino-Alcohols, Tetrahedron; 1970; 26; pp. 5247-5253.
Arend, et al., Modern Variants of the Mannich Reaction, Angew. Chem. Int. Ed.Engl.; 1998; 37; pp. 1045-1070.
Barluenga, et al., Diastereoselective Synthesis of gamma-Amino Alcohols with Three Chiral Centers by Reduction of beta-Amino Ketones and Derivatives, J. Org. Chem.; 1985; 50; pp. 4052-4056.
Brienne, et al., Reduction par l′hyrure de lithium et d′aluminium de beta-aminocetones, Bulletin de la Societe Chimique de France; 1969; 7: pp. 2395-2407.
Cicchi, et al., Synthesis of New Enantiopure gamma-aminoalcohols: their use as catalysts in the Alkylation of Benzaldehyde by Diethylzinc, Tetrahedron: Asymmetry; 1997; 8; 2; pp. 293-301.
Couturier, et al., Palladium Catalyzed Activation of Borane-amine Adducts: Rate Enhancement of Amine-borane Methanolysis in the Reduction of Nitrobenzenes to Anilines, Tetrahedron Letters; 2001; 42; pp. 2285-2288.
Denmark, et al., Catalytic Enantioselective Mannich-Type Reactions, Comprehensive Asymmetric Catalysis; Springer-Verlag:New York; 1999, vol. 2; Chapter 26.2.9; pp. 954-958.
Groger, et al., The Application of L-Proline as an Enzyme Mimic and Further New Asymmetric Using Small Organic Molecules as Chiral Catalysts, Agnew. Chem. Int. Ed.; 2001; 40; 3; pp. 529-532.
Ishitani, et al., Enantioselective Mannich-Type Reactions Using a Novel Chiral Zirconium Catalyst for the Synthesis of Optically Active beta-Amino Acid Derivatives, J. Am. Chem Soc.; 2000; 122, pp. 8180-8186.
Jiang, et al., Highly Enantioselective Reduction of Achiral Ketones with NaBH4/Me3SiCl Catalyzed by (S)-alpha,alpha-diphenylpyrrolidinemethanol, tetrahedron Letters; 2000; 41; pp. 10281-10283.
List, Benjamin, The Direct Catalytic As

Affiliated with

Also associated with

Rating

Optically active β-aminoketones, optically active... 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 β-aminoketones, optically active..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Optically active β-aminoketones, optically active... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3811530