Paramagnetic 1H-NMR relaxation probes of stereoselectivity in metalloporphyrin catalyzed olefin epoxidation

Chirality

Volumn 10, Issue 1-2, 1998, Pages 106-119

  Groves, John T ^a   Crowley, Stephen J ^a   Shalyaev, Kirill V ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Chiral; Enantioselective; Mechanism; Oxidation; Porphyrin

Indexed keywords

ALKENE; METALLOPORPHYRIN; STYRENE; COPPER; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; EPOXIDE; PROTON;

ARTICLE; CHIRALITY; EPOXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; CATALYSIS; CHEMISTRY; CONFORMATION; ELECTRON SPIN RESONANCE; GAS CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

ALKENES; CATALYSIS; CHROMATOGRAPHY, GAS; COPPER; ELECTRON SPIN RESONANCE SPECTROSCOPY; EPOXY COMPOUNDS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; METALLOPORPHYRINS; MOLECULAR CONFORMATION; PROTONS; STEREOISOMERISM;

EID: 0031594580     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.18     Document Type: Article

References (77)

1. (a) Halpern, J. In: Asymmetric Synthesis. Morrison, J.D., ed. New York: Academic Press, 1985.
2. (b) Landis, C.R., Halpern, J. Asymmetric hydrogenation of methyl-(Z) - acetamidocinnamate catalyzed by {1,2-bis((phenyl-o-anysoyl)phosphino)ethane} rhodium(I): kinetics, mechanism, and origin of enantioselection. J. Am. Chem. Soc. 109: 1746-1754, 1987.
3. Knowles, W.S., Vineyard, B.D., Sabacky, M.J., Stults, B.R. In: Fundamental Research in Homogeneous Catalysis. Tsutsui, M., ed. New York: Plenum Press, 1979:537.
4. Johnson, R.A., Sharpless, K.B. In: Catalytic Asymmetric Synthesis. Ojima, I., ed. New York: VCH, 1993.
5. Brandes, B.D., Jacobsen, E.N. Highly enantioselective, catalytic epoxidation of trisubstituted olefins. J. Org. Chem. 59:4378-4380, 1994, and references therein.
6. Kolb, H.C., VanNieuwenzhe, M.S., Sharpless, K.B. Catalytic asymmetric dihydroxylation. Chem. Rev. 94:2483, 1994.
7. Noyori, R. Chiral metal complexes as discriminating molecular catalysts. Science 248:1194, 1990.
8. Collman, J.P., Zhang, X., Lee, V.J., Uffelman, E.S., Brauman, J.I. Regioselective and enantioselective epoxidation catalyzed by metalloporphyrins. Science 261:1404, 1993.
9. (a) Schurig, V., Betschinger, F. Metal-mediated enantioselective access to unfunctionalized aliphatic oxiranes: prochiral and chiral recognition. Chem. Rev. 92:873, 1992.
10. (b) Naruta, Y. In: Metalloporphyrins in Catalytic Oxidations. Sheldon, R.A., ed. New York: M. Dekker, 1994.
11. Groves, J.T., Han, Y., Van Engen, D. Coordination of styrene oxide to a sterically hindered ruthenium(II) porphyrin. J. Chem. Soc. Chem. Commun. 436, 1990.
12. Groves, J.T., Nemo, T.E. Epoxidation reactions catalyzed by iron porphyrins. Oxygen transfer from iodsylbenzene. J. Am. Chem. Soc. 105: 5786, 1983.
13. 2 torsional terms. J. Am. Chem. Soc. 99:8127-8134, 1977.
14. Groves, J.T., Myers, R.S. Catalytic asymmetric epoxidations with chiral iron porphyrins. J. Am. Chem. Soc. 105:5791-5796, 1983.
15. Renaud, J.P., Battioni, P., Mansuy, D. Synthesis and properties of 'picket' and 'basket handle' iron-porphyrins bearing optically active amino acids close to the metallic center. New J. Chim. 11:279-290, 1987.
16. Pfeiffer, H.-P., Sander, H., Breitmaier, E. Chirale lattenzaumporphyrine. Liebigs Ann. Chem. 725-726, 1987.
17. Collman, J.P., Gagne, R.R., Reed, C.A., Halbert, T.R., Lang, G., Robinson, W.T. "Picket fence porphyrins." Synthetic models for oxygen binding hemoproteins. J. Am. Chem. Soc. 97:1427-39, 1975.
18. Groves, J.T., Viski, P. Asymmetric hydroxylation, epoxidation and sulf-oxidation catalyzed by vaulted binaphthyl metalloporphyrins. J. Org. Chem. 55:3628-3634, 1990.
19. Bucher, J.W., Lay, K.L. Metal complexes of tetrapyrrole ligands, XIV. Iron porphodimethenes: sterically and electronically modified hemes and hemins. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 30B:385-392, 1975.
20. Adler, A.D., Longo, F.R., Finarelly, J.D., Goldmacher, J., Assour, J., Korsakoff, L. A simplified synthesis for meso-tetraphenyl porphyrin. J. Org. Chem. 32:476, 1967.
21. Wagner, R.W., Lawrence, D.S., Lindsey, J.S. An improved synthesis of tetramesitylporphyrin. Tetrahedron Lett. 28:3069-3070, 1987.
22. Larrow, J.F., Jacobsen, E.N., Gao, Y., Hong, Y., Nie, X., Zepp, C.M. A practical method for the large-scale preparation of [NN′-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)] manganese(III) chloride, a highly enantioselective epoxidation catalyst. J. Org. Chem. 59: 1939-1942, 1994.
23. Schmeisser, M., Dahmen, K., Sartori, P. Perflouracyloxy-Verbindungen des positiven Jods. Chem. Ber. 100:1633-1637, 1967.
24. Collman, J.P. Caution for researchers using PFIB. Chem. Eng. News 63:2, 1985 (Letter to editor).
25. Traylor, P.S., Dolphin, D., Traylor, T.G. Sterically protected hemins with electronegative substituents: efficient catalysts for hydroxylation and epoxidation. J. Chem. Soc. Chem. Commun. 279, 1984.
26. Lucas, H.J., Kennedy, E.R., Formo, M.W. Iodosobenzene. Org. Syn., Coll. Vol. 3, 1955, 483.
27. Schurig, V., Weber, R. Use of glass and fused-silica open tubular columns for the separation of structural, configurational and optical isomers by selective complexation gas chromatography. J. Chromatogr. 289:325, 1984.
28. Groves, J.T., Han, Y.-Z. In: Cytochrome P-450: Structure, Mechanism and Biochemistry. Ortiz de Montellano, P., ed. New York: Plenum Press, 1985.
29. Groves J.T., Haushalter, R.C., Nakamura, M., Nemo, T.E., Evans, B.J. High-valent iron-porphyrin complexes related to peroxidase and cytochrome P-450. J. Am. Chem. Soc. 103:2884-2886, 1981.
30. (a) Yamamoto, S., Teraoka, J., Kashiwagi, H. Ab initio RHF and CASSCF studies on Fe-O bond in high-valent iron-oxoporphyrins. J. Chem. Phys. 88:303-312, 1988.
31. (b) Hanson, L.K., Chang, C.K., Davis, M.S., Fajer, J. Electron pathways in catalase and peroxidase enzymic catalysis. Metal and macrocycle oxidations of iron porphyrins and chlorins. J. Am. Chem. Soc. 103:663-670, 1981.
32. (c) Loew, G.H., Kert, C.J., Hjelmeland, L.M., Kirchner, R.F. Active site models of Horseradish Peroxidase compound I and a cytochrome P450 analogue: electronic structure and electric field gradients. J. Am. Chem. Soc. 99:3534-3530, 1977.
33. Bruice, T.C., Ostovic, D. Transition-state geometry in epoxidation by iron-oxo porphyrin at the compound I oxidation level. Epoxidation of alkenes catalyzed by a sterically hindered (meso-tetrakis(2,6-dibromophenyl)porphinato)iron(III) chloride. J. Am. Chem. Soc. 110: 6906-6908, 1988.
34. (a) Dunitz, J.D. Philos. Trans. R. Soc. London, Ser. B 272:99-108, 1975.
35. (b) Burgi, H.B., Dunitz, J.D., Lehn, J.M., Wipff, G. Stereochemistry of reaction paths at carbonyl centers. Tetrahedron 30:1563-1572, 1974.
36. (c) Streitwieser, A., Jr., Owens, P.H. Orbital and Electron Density Diagrams: An Application of Computer Graphics. New York: The Macmillian Company, 1973.
37. Mansuy, D., Battioni, P., Renaud, J.P., Guerin, P. Asymmetric epoxidation of alkenes catalyzed by a 'basket-handle' iron-porphyrin bearing amino acids. J. Chem. Soc. Chem. Commun. 155-156, 1985.
38. (a) Fontecave, M., Mansuy, D. Alkene epoxidation by iodosylbenzene catalyzed by porphyrin and non-porphyrin iron complexes: the importance of the porphyrin ligand in cytochrome P-450 and heme model reactions. J. Chem. Soc. Chem. Commun. 879-881, 1984.
39. (b) VanAtta, R.B., Franklin, C.C., Valentine, J.S. Oxygenation of organic substrates by iodosylbenzene catalyzed by soluble manganese, iron, cobalt, or copper salts in acetonitrile. Inorg. Chem. 23:4120, 1984.
40. (c) Franklin, C.C., VanAtta, R.B., Tai, A.F., Valentine, J.S. Copper ion mediated epoxidation of olefins by iodosylbenzene. J. Am. Chem. Soc. 106:814-816, 1984.
41. (d) Tai, A.F., Margerum, L.D., Valentine, J.S. Epoxidation of olefins by iodosylbenzene catalyzed by binuclear copper(II) complexes. J. Am. Chem. Soc. 108:5006-5008, 1986.
42. (e) Murugesan, N., Ehrenfeld, G.M., Hecht, S.M. Oxygen transfer from bleomycin-metal complexes. J. Biol. Chem. 257:8600-8603, 1982.
43. (f) Murugesan, N., Hecht, S.M. Bleomycin as an oxene transferase. Catalytic oxygen transfer to olefins. J. Am. Chem. Soc. 107:493, 1985.
44. (g) Ehrenfeld, G.M., Murugesan, N., Hecht, S.M. Activation of oxygen and mediation of DNA degradation by manganese-bleomycin. Inorg. Chem. 23:1496, 1984.
45. (h) Moriarty, R.M., Penmasta, R., Prakash, I. Possible role of Lewis acid catalysis in the oxidation of alkenes and unsaturated ketones using bleomycin-Zn(II) and bleomycin-Fe(III)-iodosylbenzene in aqueous methanol. Tetrahedron Lett. 26:4699-4702, 1985.
46. (i) Muller, P., Godoy, J. Ru-catalyzed oxidations with iodosylbenzene derivatives. Substituent effects on selectivity in oxidation of sulfides and alcohols. Helv. Chem. Acta. 66:1790, 1983.
47. (j) Srinivasan, K., Michaud, P., Kochi, J.K. Epoxidation of olefins with cationic (salen)Mn(III) complexes. The modulation of catalytic activity by substituents. J. Am. Chem. Soc. 108:2309-2320, 1986.
48. (k) Sidall, T.L., Miyaura, N., Huffman, J.C., Kochi, J.K. Isolation and molecular structure of unusual oxochromium(V) cations for the catalytic epoxidation of alkenes. J. Chem. Soc. Chem. Commun. 1185, 1983.
49. (l) Samsel, E.G., Srinivasan, K., Kochi, J.K. Mechanism of the chromium-catalyzed epoxidation of olefins. Role of oxochromium(V) cations. J. Am. Chem. Soc. 107:7606, 1985.
50. (m) Srinivasan, K., Kochi, J.K. Synthesis and molecular structure of oxochromium(V) cations. Coordination with donor ligands. Inorg. Chem. 24:4671, 1985.
51. Groves, J.T., Viski, P. Asymmetric hydroxylation by a chiral iron porphyrin. J. Am. Chem. Soc. 111:8537-8538, 1989.
52. Groves, J.T., Watanabe, Y. On the mechanism of olefin epoxidation by oxo-iron porphyrins. Direct observation of an intermediate. J. Am. Chem. Soc. 108:507-508, 1986.
53. (a) Meade, T.J., Kwik, W.-L., Herron, N., Alcock, N.W., Busch, D.H. Hydrophobic, regiospecific guest binding by transition-metal host complexes having permanent voids as revealed by FT-NMR relaxation studies. J. Am. Chem. Soc. 108:1746, 1986.
54. (b) Meade, T.J., Takeuchi, K.J., Busch, D.H. An inclusion complex containing the dioxygen molecule and an organic guest molecule cohabiting within a vaulted cobalt(II) cyclidene host - a rare kind of ternary complex. J. Am. Chem. Soc. 109:725, 1987.
55. (c) Meade, T.J., Alcock, N.W., Busch, D.H. Inclusion complex formation involving a new class of transition-metal host. Inorg. Chem. 29:3766, 1990.
56. (a) Mildvan, A.S., Gupta, R.K. Nuclear relaxation measurements of the geometry of enzyme-bound substrates and analogs. Methods Enzymol. 49:322, 1978.
57. 5. Mol. Pharm. 21:701, 1982.
58. 1H NMR comparison of the met-cyano complexes of elephant and sperm whale myoglobin. J. Biol. Chem. 259:8826, 1984.
59. 3-oxotriruthenium hexacarboxylatecumene hydroperoxide interaction. J. Oxidat. Commun. 1:295, 1980.
60. (e) Trzeciak, A.M., Zioekovski, J. Application of NMR in studies of elementary interactions in the catalytic oxidation reactions of hydrocarbons. J. Mol. Catal. 39:85, 1987.
61. 13C relaxation effects of Cu(II) paramagnetic ion in the conformational analysis of Lasalocid (antibiotic X-537 A). Spin-lattice and transverse relaxation times comparisons. Nouv. J. Chim. 4:315, 1980.
62. Dumas, P., Guerin, P. Etude des interactions des oxirannes et thiirannes avec les α,β,γ,δ-tétraphénylporphyrínes au cadmium, zinc et magnésium. Can. J. Chem. 56:925-930, 1978.
63. Groves, J.T., Ahn, K-H., Quinn, R. Cis-trans isomerization of epoxides catalyzed by ruthenium(II) porphyrins. J. Am. Chem. Soc. 110:4217-4220, 1988.
64. (a) Espersen, W.G., Hutton, W.C., Chow, S.T., Martin, R.B. Cautions concerning uses of copper(II) selective broadening in nuclear magnetic resonance spectroscopy for determination of ligand binding sites. J. Am. Chem. Soc. 96:8111, 1974.
65. (b) Eisinger, J., Shulman, R.G., Szymanski, B.M. Transition metal binding in DNA solutions. J. Chem. Phys. 36:1721, 1962.
66. 17O in aqueous solutions of paramagnetic cations and the lifetime of water molecules in the first coordination sphere. J. Chem. Phys. 37:307, 1962.
67. (d) Codrington, R.S., Bloembergen, N.J. Overhauser effect in manganese solutions in low magnetic fields. J. Chem. Phys. 29:600, 1958.
68. (e) Bloembergen, N.J. Proton relaxation times in paramagnetic solutions. J. Chem. Phys. 27:572, 1957.
69. (f) Solomon, I., Bloembergen, N.J. Nuclear magnetic interactions in the HF molecule. J. Chem. Phys. 27:572, 1956.
70. (g) Solomon, I. Phys. Rev. 99:559, 1955.
71. Ahn, K.-H. The Catalytic Reactivities of Iron and Ruthenium Porphyrins in Epoxidation, Epoxide Isomerization, Olefin Formation and Hydroxylation. Ph.D. Thesis Princeton University, Princeton, NJ, 1987:39.
72. Jacobsen, E.N., Zhang, W., Muci, A.R, Ecker, J.R., Deng, L. Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane. J. Am. Chem. Soc. 113:7063-7064, 1991.
73. Groves, J.T., Lee, J., Marla, S.S. Detection and characterization of an oxomanganese(V) porphyrin complex by rapid-Mixing stopped-flow spectrophotomotry. Formation of an oxoMn(V) porphyrin with hypochlorite has recently been demonstrated. Am. Chem. Soc. 1997, 119 (in press).
74. Norrby, P.-O., Linde, C., Bjorn, Å. On the chirality transfer in the epoxidation of alkenes catalyzed by Mn(salen) complexes. J. Am. Chem. Soc. 117:11035-11036, 1995.
75. Schurig, V., Weber, R. Manganese(II)-bis(3-heptafluorobutyryl-1R-camphorate): a versatile agent for the resolution of racemic cyclic ethers by complexation gas chromatography. J. Chromatogr. 217:51-70, 1981.
76. Bernassau, J.-M., Hyafil, F. Choice of delay time sequence on spin-lattice relaxation time measurements by inversion-recovery. J. Magn. Res. 40:245-258, 1980.
77. Sorrell, T.N. (Dioxygen) (N-methylimidazole)[(all-cis)-5,10,15,20-tetrakis[2-(2,2-dimethylpropionamido)- phenyl]porphyrinato(2-)] iron(II). Inorg. Synthesis 20:161-169, 1980.