Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2008-12-19
2010-12-28
Davis, Brian J (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S880000, C568S881000, C204S157620
Reexamination Certificate
active
07858831
ABSTRACT:
This invention is directed to a method of performing a stereoselective reaction without use of a solvent comprising contacting a reactant with a chiral reagent under sonication conditions to form an excess of an enantiomer.
REFERENCES:
Toukoniitty et al., Ultrasonics Sonochemistry (2006), 13, p. 68-75.
U.S. Appl. No. 61/016,297, filed Dec. 21, 2007, Meyer et al.
Asano et al., “Activation and Reaction Volumes in Solution,”Chem. Rev., (1978) 78:407-489.
Bian et al., “Reductive coupling of aromatic aldehydes using zinc powder in aqueous sodium hydroxide under ultrasound,”Chinese Journal of Synthetic Chemistry, (2004) 12(5):429-431.
Brown et al., “Ultrasonics in Organoborane Chemistry, A Novel and Powerful Method for Rapid Hydroboration,”Tetrahedron Lett., (1985) 26:2187-2190.
Brown et al., “The boron approach to asymmetric synthesis,”Pure&Appl. Chem., (1991) 63(3):307-316.
Canet et al., “Enantiomeric Analysis in a Polypeptide Lyotropic Liquid Crystal by Deuterium NMR,”J. Am. Chem. Soc., (1995) 117:6520-6526.
Chen et al., “Study of Chiral Auxiliaries for the Intrmolecular [2+2] Cycloaddition of a Keteniminium Salt to an Olefinic Double Bond. An New Asymmetric Synthesis of Cyclobutanones,”Tetrahedron Letters, (1990) 31(31):4467-4470.
Cherest et al., “Torsional Strain Involving Partial Bonds. The Stereochemistry of the Lithium Aluminum Hydride Reduction of Some Simple Open-Chain Ketones,”Tetrahedron Lett., (1968) 9:2199-2204.
Fan et al., “A Mild and Efficient Asymmetric Hetero-Diels—Alder Reaction of the Brassard Diene with Aldehydes ,”Eur. J. Org. Chem., (2005), 3542-3552.
Flannigan et al., “Measurement of Pressure and Density Inside a Single Sonoluminescing Bubble,”Phys. Rev. Lett., (2006) 96:204301-1-204301-4.
Flint et al., “The Temperature of Cavitation,”Science, (1991), 253:1397-1399.
Fujikawa et al., “Effects of the Non-equilibrium Condensation of Vapor on the Pressure Wave Produced by the Collapse of a Bubble in a Liquid,”J. Fluid Mech., (1980), 97:481-512.
Hickenboth et al., “Biasing Reaction Pathways with Mechanical Force,”Nature, (2007), 446:423-427.
Jenner, G., “High Pressure and Selectivity in Organic Reactions,”Tetraheron, (1997), 53:2669-2695.
Jenner, G. “Comparative Acivation Modes in Organic Synthesis. The Specific Role of High Pressure.”Tetrahedron, (2002), 58:5185-5202.
Katsuki et al., “The First Practical Method for Asymmetric Epoxidation,”J. Am. Chem. Soc., (1980), 102:5974-5976.
Kawashima et al., “Sonochemical and triethylborane-induced tin deuteride reduction for the highly stereoselective synthesis of (2′R)-[2′-2H]-2′-deoxyribonucleosides from 2′-functionalized ribonucleosides,”Tetrahedron Letters, (1993), 34(8):1317-20.
Li et al., “Aluminum/fluoride salt-mediated reductive coupling of aromatic aldehydes in aqueous media under ultrasound irradiation,”Chinese J. of Organic Chemistry, (2005), 25(12):1583-1586.
Lindley et al., “Sonochemistry Part 2—Synthetic Applications,”Chem. Soc. Rev.(1987), 16:275-311.
Liu et al., “Chiral oxazaborolidine-aluminum bromide complexes are unusually powerful and effective catalysts for enantioselective Diels-Alder reactions” (2007)J. Am. Chem. Soc.129:1498-1499.
Luche et al., “Can sonication modify the region- and steroselictivities of organic reactions?”Advances in Sonochemistry, (1999), 5:147-174.
Matsuda et al., “Ultrasonic Effects on Electroorganic Processes. Product-selectivity in Electroreduction of Benzaldehydes,”Chemistry Letter, (1994), (9):1619-22.
Matsumoto, K., “Organic Synthesis under High Pressure II,”Synthesis, (1985), 999-1027.
McDougal et al., “Asymmetric Morita-Baylis-Hillman Reactions Catalyzed by Chiral Brønsted Acids,”J. Am. Chem. Soc., (2003), 125:12094-12095.
Meddour et al., “Observation of Enantiomers, Chiral by Virtue of Isotopic Substitution, through Deuterium NMR in a Polypeptide Liquid Crystal,”J. Am. Chem. Soc., (1994), 116:9652-9656.
Midland et al., “Asymmetric Reductions of Propargyl Ketones,”Tetrahedron, (1984), 40:1371-1380.
Midland et al., “Asymmetric Reductions of Prochiral Ketones withB-3-Pinany1-9-borabicyclo[3,3.1]nonane (Alpine-Borande) at Elevated Pressures,”J. Org. Chem., (1989) 54:159-165.
Mirza-Aghayan et al., “Ultrasound Irradiation Effects on the Asymmetric Michael Reaction,”Tetrahedron Asymmetry, (1995), 6(11):2643-2646.
Northrup et al., “The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes,”J. Am. Chem. Soc., (2002) 124:6798-6799.
Parker et al., “Asymmetric Reduction. A Convenient Method for the Reduction of Alkynyl Ketones,”J. Org. Chem., (1996) 61:3214-3217.
Pihko et al., “Effect of Additives on the ProlineCatalyzed Ketone-Aldehyde Aldol Reactions,”Tetrahedron, (2006) 62:317-328.
Poisson et al., “Organocatalytic enantioselective protonation of silyl enolates mediated by cinchona alkaloids and a latent source of HF,”Angew. Chem. Int. Ed., (2007) 46:7090-7093.
Suslick et al., “Sonochemistry and Sonocatalysis of Iron Carbonyls,”J. Am. Chem. Soc., (1981), 103:7342-7344.
Suslick et al., “Sonochemistry and Sonocatalysis of Metal Carbonyls,”J. Am. Chem. Soc., (1983), 105:5781-5785.
Suslick et al., “Sonochemistry,”Science, (1990), 247:1439-1445.
Suslick et al., “The Sonochemical Hot Spot,”J. Am. Chem. Soc., (1986), 108:5641-5642.
Thayumanavan et al., “Amine-Catalyzed Direct DielsAlder Reactions of αβ-Unsaturated Ketones with Nitro Olefins,”Tetrahedron Lett., (2002), 43:3817-3820.
Tietze et al., “Intermolecular Hetero-Diels-Alder Reactions of Enamino Ketones at High Pressure. The First Significant Pressure-Induced Diastereoselectivity in Organic Transformations,”J. Am. Chem. Soc., (1988), 110:4065-4066.
Trost et al., “Direct asymmetric aldol reactions of acetone using bimetallic zinc catalysts,”Org. Lett., (2001) 3(16):2497-2500.
Tsukinoki et al., “Preparation of benzyl-.alpha.-D1-alcohol by reduction of benzaldehyde with Raney alloys in an alkaline deuterium oxide solution,”Journal of Labelled Compounds and Radiopharmaceuticals, (1993), 33(10):987-90.
Tuncay et al., “Ultrasound Promoted Hypervalent Iodine Reactions: α-Tosyloxylation of Ketones with [Hydroxy(Toxyloxy)Iodo]Benzene,”Tetrahedron Lett., (1992), 33, 7647-7650.
Wang et al., “An Efficient Catalytic Asymmetric Epoxidation Method,”J. Am. Chem. Soc., (1997) 119(46):11224-11235.
West et al., “A Mechanistic Probe for Asymmetric Reactions: Deuterium Isotope Effects at Enantiotopic Groups,”J. Am. Chem. Soc., (2008), 130:7816-7817.
Yamamoto et al., “Aldol Reaction of Silyl Enol Ethers Under Neutral Conditions,”J. Am. Chem. Soc.(1983), 105:6963-6965.
Zeynizadeh et al, “Reduction of carbonyl compounds with NaBH4 under ultrasound irradiation and conditions,” Zeitschrift fuer Naturforschung,B:Chemical Sciences, (2004), 59(6):704-710.
Zhang et al., “Enantioselective Epoxidation of Unfunctionalized Olefins Catalyzed by (Sa1en)manganese Complexes,”J. Am. Chem. Soc., (1990) 112:2801-2803.
Meyer Matthew P.
Zhu Hui
Davis Brian J
Foley & Lardner LLP
Konski Antoinette F.
The Regents of the University of California
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