Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2007-10-09
2007-10-09
Nazario, Porfirio (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
Reexamination Certificate
active
10569757
ABSTRACT:
The corresponding α-aminooxy ketone is manufactured with a high yield and a high enantioselectivity. A manufacturing method for an optically active α-aminooxy ketone derivative expressed by formula (1), wherein a ketone expressed by formula (2) is caused to react with a nitroso compound expressed by formula (3) in the presence of a proline derivative expressed by formula (4).In the formula, R1and R2respectively denote an alkyl, alkenyl or alkynyl group, and R1and R2may be linked to form a ring. R3denotes an aryl, heterocyclic, alkyl, alkenyl or alkynyl group. A denotes a hydrogen atom, alkoxy group, aryloxy group, acyloxy group or silyloxy group which may have a substituent.
REFERENCES:
Brown et al (J. Am. Chem. Soc., 2003, 125, 10808-10809).
Brown, Sean P., et al.,The Direct and Enantioselective Organocatalytic α-Oxidation of Aldehydes, J.Am. Chem. Soc., vol. 125, No. 36, 2003, 10808-10809.
Ohtake, Hiroaki, et al.,Regioselective Synthesis of Nitrones by Decarboxylative Oxidation of N-Alkyl-α-amino Acids and Application to the Synthesis of 1-Azabicyclic Alkaloids, Bull. Chem. Soc., Jpn., 72, No. 12 (1999) 2737-2754.
Momiyama, Norie, et al.,Catalytic Enantioselective Synthesis of α-Aminoaxy and α-Hydroxy Ketone Using Nitrosobenzene, J. Am. Chem. Soc., vol. 125, No. 20, 2003, 6038-6039.
Zhong, Guofu,A Facile and Rapid Route to Highly Enantiopure 1,2-Diols by Novel Catalytic Asymmetric α-Aminoxylation of Aldehydes, Angew. Chem. Int. Ed. 2003, 42, 4247-4250.
Hayaski, Yujiro, et al.,Direct Proline Catalyzed Asymmetric α-Aminooxylation of Aldehydes, Tetrahedron Letters 44 (2003) 8293-8296.
Davis, Franklin, et al.,Asymmetric Hydroxylation of Enolates with N-Sulfonyloxaziridines, Chem. Rev. 1992, 92, 919-934.
Davis, Franklin, et al.,Stereochemistry of the Asymmetric Oxidation of Ketone Enolates Using(Camphorylsulfonyl)oxaziridines, J. Org. Chem. 1986, 51, 4083-4085.
Chen, Bang-Chi, et al.,Enantioselective Synthesis of(+) -Kjellmanianone, Tetrahedron vol. 47, No. 2, 173-182, 1991.
Davis, Franklin, et al.,Kinetic Resolution in the Asymmetric Hydroxylation of Enolates. Stereospecific Synthesis of(2S,3R)-(-)-Verrucarinolactone, J. Org. Chem., 1992, 57, 3337-3339.
Davis, Franklin, et al.,Chemistry of Oxaziridines. 18. Synthesis and Enantioselective Oxidations of the [(8,8-Dihalocamphoryl)sulfonyl]oxaziridines1.2,J. Org. Chem. 1992, 57, 7274-7285.
Davis, Franklin, et al.,Hydroxylation of Dihydroisoxazoles Using N-Sulfonyloxaziridines, J. Org. Chem. 1993, 58, 7591-7593.
Davis, Franklin, et al.,Asymmetric Synthesis of the AB Ring Segments of Daunomycin and 4-Demethoxydaunomycin, J. Org. Chem. 1994, 59, 1184-1190.
Morikawa, Kouhei, et al.,Catalytic Asymmetric Dihydroxylation of Tetrasubstituted Olefins, J. Am. Chem. Soc. 1993, 115, 8463-8464.
Hashiyama, Tomiki, et al.,α-Hydroxy Ketones in High Enantiomeric Purity from Asymmetric Dihydroxylation of Enol Ethers, J. Org. Chem. 1992, 57, 5067-5068.
Fukuda, Tsutomu, et al.,Mn-Salen Catalyzed Asymmetric Oxidation of Enol Derivatives, Tetrahedron Letters, vol. 37, No. 25, 4389-4392, 1996.
Adam, Waldemar, et al.,Synthesis of Optically Active α-Hydroxy Carbonyl Compounds by the Catalytic, Enantioselective Oxidation of Silyl Enol Ethers and Ketene Acetals with(Salen)manganese(III)Complexes, J. Am. Chem. Soc. 1998, 120, 708-714.
Zhu, Yuanming, et al.,High Enantioselective Epoxidation of Enol Silyl Ethers and Esters, Tetrahedron Letters 39 (1998) 7819-7822.
Adam, Waldemar, et al.,Synthesis of optically active α-hydroxy ketones by enantioselective oxidation of silyl enol ethers with a fructose-derived dioxirane, Tetrahedron: Asymmetry 9 (1998) 397-401.
Hayashi, et al., “Direct Proline-Catalyzed Asymmetric Alpha-Aminoxylation of Ketones”, Angew. Chem. Int. Ed. 2004, 43, pp. 1112-1115.
Bogevig, et al., “Direct Catalytic Enantioselective Synthesis Alpha-Aminoxylation of Keytones: A Stereoselective Synthesis of Alpha-Hydroxy and Alpha, Alpha′-Dihydroxy Ketones”, Angew. Chem. Int. Ed. 2004, pp. 1109-1112.
Cordova, et al., “The Direct Catalytic Asymmetric Alpha-Aminooxylation Reaction: Development of Stereoselective Routes to 1,2-Diols and 1,2-Amino Alcohols and Density Functional Calculations”, Chem. Eur. J. 2004, 10, pp. 3673-3684.
Hayashi Yujiro
Shoji Mitsuru
Deveau Todd
Gale Kellette
Nazario Porfirio
Thomas Kayden Horstemeyer & Risley LLP
Tokyo University of Science, Center for Science and Technology E
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