Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2005-02-08
2005-02-08
Shippen, Michael L. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S060000, C568S811000, C568S860000
Reexamination Certificate
active
06852874
ABSTRACT:
A process for catalyzing asymmetric dihydroxylations of olefins employs an Os(VI) complex as a catalytic intermediate in the formation of chiral vicinal diol products. The process requires a chiral bidentate ligand that favors diol formation in the “second cycle” of asymmetric dihydroxylation.
REFERENCES:
patent: 4965364 (1990-10-01), Marko
patent: 5516929 (1996-05-01), Sharpless
patent: 6297186 (2001-10-01), Kobayashi
patent: 6387033 (2002-05-01), Choudary
patent: WO-8902428 (1989-03-01), None
Jacobsen, et al., “Asymmetric Dihydroxylation via Ligand-Accelerated Catalysis”,J. Am. Chem. Soc. 110: 1968-1970 (1988).
Jacobsen, et al., “Kinetic Role of the Alkaloid Ligands in Asymmetric Dihydroxylation”,J. Am. Chem. Soc. 111: 737-739 (1989).
Wai, J. S. M., et al., “A Mechanistic Insight Leads to a Greatly Improved Osmium-Catalyzed Asymmetric Dihydroxylation Process”,J. Am. Chem. Soc. 111: 1123-1125 (1989).
Lohray, et al., “Documenting the Scope of the Catalytic Asymmetric Dihydroxylation”,Tetrahedron Lett. 30: 2041-2044 (1989).
Kwong, et al., “Preclusion of the ‘Second Cycle’ in the Osmium-Catalyzed Asymmetric Dihydroxylation of Olefins Leads to a Superior Process”,Tetrahedron Lett. 31: 2999-3002 (1990).
Sharpless, et al., “The Osmium-Catalyzed Asymmetric Dihydroxylation: A New Ligand Class and a Process Improvement”,J. Org. Chem. 57: 2768-2771 (1992).
Morikawa, et al., “Catalytic Asymmetric Dihydroxylation of Tetrasubstituted Olefins”,J. Am. Chem. Soc. 115: 8463-8464 (1993).
Kolb, et al., “Catalytic Asymmetric Dihydroxylation”,Chem. Rev. 94: 2483-2547 (1994).
Norrby, et al., “Toward an Understanding of the High Enantioselectivity in the Osmium-Catalyzed Asymmetric Dihydroxylation. 3. New Insights into Isomeric Forms of the Putative Osmaoxetane Intermediate”,J. Am. Chem. Soc. 118: 35-42 (1996).
Rudolph, et al., “Smaller Substituents on Nitrogen Facilitate the Osmium-Catalyzed Asymmetric Aminohydroxylation”,Angew. Chem. Int. Ed. Engl. 35: 2810-2813 (1996).
DelMonte, et al., “Experimental and Theoretical Kinetic Isotope Effects for Asymmetric Dihydroxylation. Evidence Supporting a Rate-Limiting “(3+2)” Cycloaddition”,J. Am. Chem. Soc. 119: 9907-9908 (1997).
Kolb, H. C.; Sharpless, K. B. “Asymmetric Dihydroxylation” in “Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals”, vol. 2, Wiley-VCH; New York, 1998: Beller, M.; Bolm, C., Eds. pp. 219-242.
Kolb, H. C.; Sharpless, K. B. “Asymmetric Aminohydroxylation” in “Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals”, vol. 2, Wiley-VCH; New York, 1998: Beller, M.; Bolm, C., Eds. pp. 243-260.
Andersson Malin
Epple Robert
Fokin Valery
Sharpless K. Barry
Lewis Donald G.
Shippen Michael L.
The Scripps Research Institute
LandOfFree
Second cycle asymmetric dihydroxylation reaction does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Second cycle asymmetric dihydroxylation reaction, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Second cycle asymmetric dihydroxylation reaction will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3477782