Method for producing optically active aziridine compounds...

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

Reexamination Certificate

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C568S592000

Reexamination Certificate

active

07897819

ABSTRACT:
This invention provides a method for producing an optically active aziridine compound or amine compound, which uses as a catalyst a Ru(salen)(CO) complex represented by the following formula (I) or its enantiomer having a high stability, in a high turnover number (TON) and a high enantioselectivity. In the formula (I), Ar is represented by the following formula (VI) or (VII), wherein in the formula (VI), Xs are independently a halogen or a halogenated alkyl group and R1and R2s are independently hydrogen or an alkyl group or a trialkylsilyl group having a carbon number of 1-4, and in the formula (VII), R3is a bulky group.

REFERENCES:
patent: 1 449 831 (2004-08-01), None
patent: A-2002-080415 (2002-03-01), None
Kawabata et al., “Construction of Robust Ru-Salen Complex and Asymmetric Aziridination with Azide Compounds as Nitrene Precursor,”The Chemical Society of Japan, vol. 85, No. 2, Mar. 11, 2005, p. 1091. (w/ Abstract).
Omura et al., “Design of a robust Ru(salen) complex: aziridination with improved turnover number usingN-arylsulfonyl azides as precursors,”Chemical Communications, No. 18, Sep. 21, 2004, pp. 2060-2061.
Omura et al., “Asymmetric Aziridnation and Regioselective Amination Using Azide Compound as a Nitrene Precursor,” vol. 36, Oct. 20, 2003, pp. 50-52. (w/ Abstract).
Hamada et al., “Highly Enantioselective Benzylic Hydroxylation with Concave Type of (Salen)manganese(III) Complex,”Tetrahedron, vol. 54 (1998), pp. 10017-10028.
Murakami et al. “Ru(salen)-catalyzed asymmetric sulfimidation using arylsulfonyl azide.”Tetrahedron Letters. vol. 42 (2001), pp. 7071-7074.
Murakami et al. “Ru(salen)-Catalyzed Asymmetric Sulfimidation and Subsequent [2,3]Sigmatropic Rearrangement.”Chirality. vol. 15 (2003), pp. 116-123.
Omura et al. “Enantioselective Aziridination and Amination Usingp-Toluenesulfony Azide in the Presence of Ru(salen)(CO) Complex.”Chemistry Letters. vol. 32, No. 4 (2003), pp. 354-355.
Sasaki et al., “Rational Design of Mn-Salen Catalyst (2): Highly Enantionselective Epoxidation of Conjugatedcis-Olefins,”Tetrahedron, vol. 50, No. 41, pp. 11827-11838 (1994).
Uchida, Tatsuya et al. “Mechanism of asymmetric sulfimidation withN-alkoxycarbonyl azide in the presence of (OC)Ru(salen) complex,” Crest, Oct. 20, 2003, pp. 7965-7968, vol. 44, No. 43,Tetrahedron Letters, Elsevier, Amsterdam.
Apr. 27, 2010 Office Action issued in Japanese Patent Application No. 2006-528490 (with translation).
The Chemical Society of Japan, The 83rdAnnual Spring Meeting (2003), Seminar Proceeding II, 2003, p. 1199.
Jul. 20, 2010 Office Action issued in U.S. Appl. No. 12/654,824.

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