Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1996-03-25
1999-07-27
McKane, Joseph K
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
540593, 540604, 544264, 548965, 548969, 549 1, 549 90, 549296, 549513, 549518, 552 4, 564 1, 564 15, 564274, 564513, C07D20306
Patent
active
059292326
ABSTRACT:
The present invention relates to a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic chiral catalyst to produce a stereoisomerically or regioselectively enriched product.
REFERENCES:
patent: 3868401 (1975-02-01), Aratani et al.
patent: 4151195 (1979-04-01), Warnant et al.
patent: 4471130 (1984-09-01), Katsuki et al.
patent: 4538003 (1985-08-01), Tam
patent: 4565845 (1986-01-01), Inoue et al.
patent: 4594439 (1986-06-01), Katsuki et al.
patent: 4663467 (1987-05-01), Kruper, Jr. et al.
patent: 4822899 (1989-04-01), Groves et al.
patent: 4870208 (1989-09-01), Chan et al.
patent: 4885376 (1989-12-01), Verkade
patent: 4965364 (1990-10-01), Marko et al.
patent: 5093491 (1992-03-01), Ellis, Jr. et al.
patent: 5126494 (1992-06-01), Gilheany et al.
patent: 5250731 (1993-10-01), Burk
patent: 5254704 (1993-10-01), Takano et al.
patent: 5258553 (1993-11-01), Burk
patent: 5296595 (1994-03-01), Dolye
patent: 5310956 (1994-05-01), Takano et al.
patent: 5312957 (1994-05-01), Casalnuovo et al.
patent: 5321143 (1994-06-01), Sharpless et al.
patent: 5352814 (1994-10-01), Katsuki et al.
patent: 5360938 (1994-11-01), Babin et al.
Adam, W. et al. (1994) "Tridentate .beta.-Hydroperoxy Alcohols As Novel Oxygen Donors For The Titanium-Catalyzed Epoxidation of .nu.,.delta.-Unsaturated .alpha., .beta.-Diols: A Direct Diastereoselective Synthesis Of Epoxy Diols" Angew Chem Int Ed Engl 33(10):1170-1108.
Agarwal, D. et al. (1992) "Olefin Epoxidation Using Iron (III) Schiff Base Complexes As Catalyst" Indian Journal of Chemistry 31A:785-787.
Barili, P et al. (1993) "Regio- and Stereochemistry Of The Acid Catalyzed And Of A Highly Enantioselective Enzymatic Hydrolysis of some Epoxyterahydrofurans" Tetrahedron 49(28):6263-6276.
Brandes, B. and E. Jacobsen (1994) "Highly Enantioselective, Catalytic Epoxidation Of Trisubstituted Olefins" J. of Am. Chem. Soc. 59:4378-80.
Chang, S. et al. (1994) "Effect of Chiral Quaternary Ammonium Salts On (Salen) Mn-Catalyzed Epoxidation Of Cis-Olefins. A Highly Enantioselective, Catalytic Route to Trans-Epoxides" J. Am. Chem. Soc. 116:(15):6937-8.
Chen, X. et al. (1993) "Microbiological Transformations. 27. The First Examples for Preparative-Scale Enantioselective or Diastereoselective Epoxide Hydrolyses Using Microorganisms. An Unequivocal Access to All Four Bisabolol Stereoisomers" J. Am. Chem. Soc. 58(20):5528-32.
Collman, J. et al. (1993) "Regioselective and Enantioselective Epoxidation Catalyzed By Metalloporphyrins" Science 261:1404-1411.
Collman, J. et al. (1993) "Enantioselective Epoxidation Of Unfunctionalized Olefins Catalyzed By Threitol-Strapped Manganese Porphyrins" J. Am. Chem. Soc. 115:3834-3835.
Corey, E. and F. Hannon (1987) "Chiral Catalysts For The Enantioselective Addition Of Organometallic Reagents To Aldehydes" Tetrahedron Letters 28(44)5233-5236.
Desimoni, G. et al. (1992) "Copper(II) In Organic Synthesis. X (*). The Importance of Steric Hindrance In The Design of Chiral Tridentate Ligand Copper (II) Catalysts For Enantiosective Michael Reactions(**)" Gazzetta Chimica Italiana 122:268-273.
Emziane, M. et al. ( 1988) "Asymmetric Ring-Opening Of Cyclohexene Oxide With Trimethylsilyl Azide In The Presence Of Titanium Isopropoxide/Chiral Ligand" J. of Organometallic Chemistry 346:C7-C10.
Groves, J. and R. Neumann (1989) "Regioselective Oxidation Catalysis In Synthetic Phospholipid Vesicles. Membrane-Spanning Steroidal Metalloporphyrins" J. Am. Chem. Soc. 111:2900-2909.
Groves, J. and R. Neumann (1987) "Membrane-Spanning Steroidal Metalloporphyrins as Site-Selective Catalysts in Synthetic Vesicles" J. Am. Chem. Soc. 109:5045-5047.
Jameson, D. (1990) "2,6-Bis(N-pyrazolyl)pyridines: The Convenient Synthesis of a Famity of Planar Tridentate N3 Ligands that are Terpyridine Analogues" J. Org. Chem. 55:4992-4994.
Jacobsen, E. et al. (1991) "Highly Enantioselective Epoxidation Catalysts Derived From 1,2-Diaminocyclohexane" J. Am. Chem. Soc. 113:7063-7064.
Knebel, W. and R. Angelici (1974) "Kinetic and Equilibrium Studies of Bi-and Tridentate Chelate Ring-Opening Reactions of Metal Carbonyl Complexes" Inorganic Chemistry 13(3):632-637.
Kruper, W. and Dellar, D. (1995) "Catalytic Formation of Cyclic Carbonates From Epoxides and CO2 With Chromium Metalloporphyrinates" J. Org. Chem. 60:725-727.
Larrow, J. and E. Jacobsen (1994) "Kinetic Resolution Of 1,2-Dihydronaphthalene Oxide And Related Epoxides Via Asymmetric C-H Hydroxylation" J. Am. Chem. Soc. 116:12129-30.
Larrow, J. and E. Jacobsen (1994) "A Practical Method For The Large-Scale N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-Cyclohexanediaminato (2-)!manganese (III) Chloride, A Highly Enantioselective Epoxidation Catalyst" J. Org. Chem. 59:1939-42.
Li, Z. et al. (1993) "Asymmetric Alkene Aziridination with Readily Available Chiral Diimine-Based Catalysts" J. Am. Chem Soc. 115(12):5326-5327.
Marangoni, G. and B. Pitteri (1993) "Crystal Structure of Cationic Square Planar Platinum(II) Complexes Containing The Tridentate Chelate Ligand 2,6-Bis(methylthiomethyl)pyridine" Polyhdron 12(13):1669-1673.
Maruoka, K et al. (1989) "An Efficient Catalytic Procedure For Epoxide Rearrangement" Tetrahedron Letters 30(41):5607-5610.
Narasaka, K. (1991) "Chiral Lewis Acids In Catalytic Asymmertric Reactions" Synthesis Jan.:1-11.
Nugent, W. et al. (1993) "Beyond Nature's Chiral Pool: Enantioselective Catalysis In Industry" Science 259:479-483.
Nugent, W. (1992) "Chiral Lewis Acid Catalysis. Enantioselective Addition of Azide to Meso Epoxides" J. Am. Chem. Soc. 114:2768-2769.
Oppolzer, W. and R. Radinov (1988) "Enantioselective Synthesis of Sec-Allylalcohols by Catalytic Asymmetric Addition Of Divinylzinc To Aldehydes" Tetrahedron Letters 29(44):5645-5648.
Ozaki, S. et al. (1990) "Synthesis Of Chiral Square Planar Cobalt(III) Complexes and Catalytic Asymmetric Epoxidations With There Complexes" J. Chem. Soc. Perkin Trans. 2 Issue 1:353-359.
Palucki, M. et al. (1994) "Highly Enantioselective, Low-Temperature Epoxidation of Styrene" J. Am. Chem. Soc. 116:9333-9334.
Palucki, A. et al. (1992) "Asymmetric Oxidation Of Sulfides With H202 Catalyzed By (Salen) Mn (III) Complexes" Tetrahedron Letters, 33(47):7111-7114.
Sasaki, H. et al. (1994) "Rational Design Of Mn-Salen Catalyst (2): Highly Enantioselective Epoxidation of Conjugated cis-Olefins" Tetrahedron 50(41):11827-11838.
Schurig, V. and F. Betschinger (1992) "Metal-Mediated Enantioselective Access to Un-functionalized Allphatic Oxiranes: Prochiral and Chiral Recognition" Chem. Rev. 92:873-888.
Srinivasan, K. et al. (1986) "Epoxidation of Olefins With Cationic (Salen) Mn III Complexes. The Modulation of Catalytic Activity By Substituents" J. Am. Chem. Soc. 108:2309-2320.
Stinson, S. (1992) "Chiral Drugs" Chemical and Chemical Engineering News Sep. 28 pp. 46-79.
Ward, R. (1990) "Non-Enzymatic Asymmetric Transformations Involving Symmetrical Bifunctional Compounds" Chem. Soc. Rev. 19:1-19.
Woolley, P. (1975) "Models For Metal Ion Function In Carbonic Anhydrase" Nature 258:677682.
Yamashita, H. (1988) "Metal(II) d-Tartrates Catalyzed Asymmetric Ring Opening Of Oxiranes With Various Nucleophiles" The Chemical Society of Japan 61:1213-1220.
Zhang, W. et al. (1990) "Enantioselective Epoxidation Of Unfunctionalized Olefins Catalyzed By (Selen)manganese Complexes" J. Am. Chem. Soc. 112:2801-2803.
Zhang, W. and E. Jacobsen (1991) "Asymmetric Olefin Epoxidation With Sodium Hypochlorite Catalyzed By Easily Preparted Chiral Mn (III) Salen Complexes" J. Org. Chem. 56:2296-2298.
Martinez, L.E. et al. (1995) "Highly enantioselective ring opening of epoxides catalized by (salen)Cr(III)complexes" J. Am. Chem Soc. 117:5897-5898.
Leighton, J.L. et al. (1996) "Efficient synthesis of (R)-4-((trimethylsilyl)oxy)-2-cyclopentenone by enantioselective catalytic epoxide ring opening" J. Org. Chem. 61:389-390.
Hayashi, M. et al. (1994) "Novel asymmetric ring-opening of symmetrical N-acylaziridines with arenethiols catalysed by chiral dialkyl tartrate-diethylzinc complexes" J.
Jacobsen Eric N.
Leighton James L.
Martinez Luis E.
Campbell Paula A.
McKane Joseph K
President and Fellows of Harvard College
Vincent Matthew P.
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