Recyclable chiral metathesis catalysts

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

Reexamination Certificate

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C556S136000, C558S357000, C558S462000, C548S103000

Reexamination Certificate

active

06939982

ABSTRACT:
The present invention relates to chiral metal catalysts for stereoselective olefin metathesis reactions, which are recyclable and reusable in such metathesis reactions. The chiral metal-based metathesis catalysts of the invention comprise multidentate optically active or racemic chiral ligands that enable their use in asymmetric synthetic processes, such as for example, in ring-opening and ring-closing metathesis reactions (ROM and RCM, respectively) of alkenes. The catalysts of the invention are organometallic complexes of multivalent metals comprising one or more chiral bidentate ligands that exhibit superior reactivity and stereoselectivity properties. The present invention also provides methods of making such catalysts and methods for utilizing them in catalyzing stereoselective olefin metathesis reactions to provide asymmetric products in relatively high enantiomeric or stereoisomeric excess.

REFERENCES:
patent: 6590048 (2003-07-01), Fürstner et al.
Copy of International Search Report, dated Oct. 20, 2003.
Garber, et al., Efficient and Recyclable Monomeric and Dendritic Ru-Based Metathesis Catalysts,Journal of the American Chemical Society, vol. 122, No. 34: 8168-8179 (2000).
Kingsbury, et al., A Recyclable Ru-Based Metathesis Catalyst,Journal of the American Chemical Society, vol. 121, No. 4: 791-799 (1998).
Gessler, et al., Synthesis and Metathesis Reactions of a Phosphine-free Dihydroimidazole Carbene Ruthenium Complex,Tetrahedron Letters, No. 51: 9973-9976 (2000).
Harrity, et al., Chromenes through Metal-Catalyzed Reactions of Styrenyl Ethers, Mechanism and Utility in Synthesis,Journal of the American Chemical Society, vol. 120, No. 10: 2343-2351 (1997).
Randl, et al., Highly Selective Cross Metathesis with Acrylonitrile Using a Phosphine Free Ru-Complex,Synlett, No. 3: 430-432 (2000).
Harrity, et al., Ru-Catalyzed Rearrangement of Styrenyl Ethers. Enantioselective Synthesis of Chromenes through Zr- and Ru-Catalyzed Processes,Journal of the American Chemical Society, vol. 119; 1488-1489 (1996).

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