Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Reexamination Certificate
2011-01-18
2011-01-18
Wilson, James O (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
Reexamination Certificate
active
07872123
ABSTRACT:
The present invention is directed to a process of making α-aminooxyketone and α-hydroxyketone compounds. The synthetic pathway involves reacting an aldehyde or ketone substrate and a nitroso substrate in the presence of a catalyst of the formula (IV):wherein Xa-Xcrepresent independently nitrogen, carbon, oxygen or sulfur and Z represents a 4 to 10-membered ring with or without a substituent and optionally a further step to convert the α-aminooxyketone compound formed to the α-hydroxyketone compound which results in α-aminooxyketone and α-hydroxyketone compounds with high enantioselectivity and high purity. The present invention is also directed to a catalytic asymmetric O-nitroso Aldol/Michael reaction involving a cyclic α,β-unsaturated ketone substrate and a nitroso substrate. This methodology involves reacting the cyclic α,β-unsaturated ketone substrate and the nitroso substrate in the presence of a proline-based catalyst, to provide a heterocyclic product.
REFERENCES:
Merino et al. Organocatalyzed Asymmetric alpha-Aminoxylation of aldehydes and ketones-An efficient access to enantiomerically pure alpha-hydroxycarbonyl compounds, diols, and even amino alcohols. 2004, Angewandte Chemie International Edition,43,2995-2997.
Yujiro Hayashi, et al., Direct Proline Catalyzed Asymmetric α-Aminooxylation Of Aldehydes, Tetrahedron Letters 44 (2003) 8293-8296.
Hiromi Torii, et al., Asymmetric Direct Aldol Reaction Assisted By Water And A Proline-Derived Tetrazole Catalyst, Angew. Chem. Int. Ed. (2004) vol. 43, 1983-1986.
Yuhei Yamamoto, et al., Enantioselective TandemO-Nitroso Aldol/Michael Reaction, J. Am. Chem. Soc. (2004) vol. 126, 5962-5963.
Momiyama Norie
Saito Susumu
Torii Hiromi
Yamamoto Hisashi
Yamamoto Yuhei
Frommer & Lawrence & Haug LLP
Japan Science and Technology Agency
McDowell Brian
Wilson James O
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