메뉴 건너뛰기




Volumn 39, Issue 1, 2006, Pages 1-9

A novel approach to the efficient oxygenation of hydrocarbons under mild conditions. Superior oxo transfer selectivity using dioxiranes

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; DIOXIRANE; EPOXIDE; OXIDIZING AGENT;

EID: 33344479001     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar050163y     Document Type: Review
Times cited : (158)

References (66)
  • 1
    • 33344478806 scopus 로고    scopus 로고
    • Goldberg, K. I., Goldman, A. S., Eds. ACS Symposium Series 885; American Chemical Society: Washington, DC
    • For instance, see: (a) Goldberg, K. I., Goldman, A. S., Eds. Activation and Functionalization of C-H Bonds; ACS Symposium Series 885; American Chemical Society: Washington, DC, 2004.
    • (2004) Activation and Functionalization of C-H Bonds
  • 2
    • 0004281404 scopus 로고
    • Hill, C. L., Ed. Wiley: New York, see references therein
    • (b) Hill, C. L., Ed. Activation and Functionalization of Alkanes; Wiley: New York, 1989; see references therein.
    • (1989) Activation and Functionalization of Alkanes
  • 3
    • 0035984571 scopus 로고    scopus 로고
    • Oxidizing species in the mechanism of cytochrome P450
    • and references therein
    • Ortiz de Montellano, P. R.; De Voss, J. J. Oxidizing species in the mechanism of cytochrome P450. Nat. Prod. Rep. 2002, 19, 477-493 and references therein.
    • (2002) Nat. Prod. Rep. , vol.19 , pp. 477-493
    • Ortiz De Montellano, P.R.1    De Voss, J.J.2
  • 6
    • 0001361409 scopus 로고    scopus 로고
    • The functionalization of saturated hydrocarbons by Gif chemistry
    • Barton, D. H. R. The functionalization of saturated hydrocarbons by Gif chemistry. NATO ASI Ser., Ser. E: Appl. Sci. 1996, 320, 589-599.
    • (1996) NATO ASI Ser., Ser. E: Appl. Sci. , vol.320 , pp. 589-599
    • Barton, D.H.R.1
  • 7
    • 0029143480 scopus 로고
    • Methyltrioxorhenium-catalyzed C-H insertion reactions of hydrogen peroxide
    • Murray, R. W.; Iyanar, K.; Chen, J.; Wearing, J. T. Methyltrioxorhenium- catalyzed C-H insertion reactions of hydrogen peroxide. Tetrahedron Lett. 1995, 36, 6415-6418.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6415-6418
    • Murray, R.W.1    Iyanar, K.2    Chen, J.3    Wearing, J.T.4
  • 9
    • 0012447426 scopus 로고
    • Catalytic oxidations with hydrogen peroxide as oxidant. the use of polyoxometalates in reactions with hydrogen peroxide
    • Hill, C. L. Catalytic oxidations with hydrogen peroxide as oxidant. The use of polyoxometalates in reactions with hydrogen peroxide. Catal. Met. Complexes 1992, 9, 253-280.
    • (1992) Catal. Met. Complexes , vol.9 , pp. 253-280
    • Hill, C.L.1
  • 10
    • 0036739958 scopus 로고    scopus 로고
    • TAML Oxidant Activators
    • Collins, T. J. TAML Oxidant Activators. Acc. Chem. Res. 2002, 35, 782-790.
    • (2002) Acc. Chem. Res. , vol.35 , pp. 782-790
    • Collins, T.J.1
  • 11
    • 33344462768 scopus 로고    scopus 로고
    • note
    • Many authors have termed "oxygenation" the net oxidation of alkanes by a given oxygen atom transfer, DO, that is, R-H + DO →R-OH + D. The name might actually refer to complex oxidation mechanisms. Although the word "oxyfunctionalization" appears more appropriate for the process, both terms will be used interchangeably in this Account.
  • 12
    • 0242498383 scopus 로고    scopus 로고
    • Mechanism of chromyl chloride alkane oxidation
    • (a) Rappe, A. K.; Jaworska, M. Mechanism of chromyl chloride alkane oxidation. J. Am. Chem. Soc. 2003, 125, 13956-13957.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 13956-13957
    • Rappe, A.K.1    Jaworska, M.2
  • 14
    • 0003678023 scopus 로고
    • ACS Monograph 186; American Chemical Society: Washington, see references therein
    • Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph 186; American Chemical Society: Washington, 1990; see references therein.
    • (1990) Oxidations in Organic Chemistry
    • Hudlicky, M.1
  • 15
    • 0001742543 scopus 로고
    • Dioxiranes: A new class of powerful oxidants
    • Adam, W.; Curci, R.; Edwards, J. O. Dioxiranes: a new class of powerful oxidants. Acc. Chem. Res. 1989, 22, 205-211.
    • (1989) Acc. Chem. Res. , vol.22 , pp. 205-211
    • Adam, W.1    Curci, R.2    Edwards, J.O.3
  • 16
    • 84948351019 scopus 로고
    • Dioxirane oxidations: Taming the reactivity-selectivity principle
    • For instance, see: (a) Curci, R.; Dinoi, A.; Rubino, M. F. Dioxirane oxidations: taming the reactivity-selectivity principle. Pure Appl. Chem. 1995, 67, 811-22.
    • (1995) Pure Appl. Chem. , vol.67 , pp. 811-822
    • Curci, R.1    Dinoi, A.2    Rubino, M.F.3
  • 17
    • 0001218439 scopus 로고
    • Dioxiranes, three-membered ring cyclic peroxides
    • Ando, W., Ed.; Wiley: New York, Chapter 4, see also references therein
    • (b) Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. Dioxiranes, three-membered ring cyclic peroxides. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992; Chapter 4, pp 195-219; see also references therein.
    • (1992) Organic Peroxides , pp. 195-219
    • Adam, W.1    Hadjiarapoglou, L.P.2    Curci, R.3    Mello, R.4
  • 18
    • 27844577489 scopus 로고
    • On the formation and reactivity of dioxirane intermediates in the reaction of peroxoanions with organic substrates
    • Edwards, J. O.; Pater, R. H.; Curci, R.; DiFuria, F. On the formation and reactivity of dioxirane intermediates in the reaction of peroxoanions with organic substrates. Photochem. Photobiol. 1979, 30, 63-70.
    • (1979) Photochem. Photobiol. , vol.30 , pp. 63-70
    • Edwards, J.O.1    Pater, R.H.2    Curci, R.3    DiFuria, F.4
  • 19
    • 4143088133 scopus 로고    scopus 로고
    • Organocatalytic asymmetric epoxidation of olefins by chiral ketones
    • (a) Shi, Y. Organocatalytic asymmetric epoxidation of olefins by chiral ketones. Acc. Chem. Res. 2004, 37, 488-496.
    • (2004) Acc. Chem. Res. , vol.37 , pp. 488-496
    • Shi, Y.1
  • 20
    • 4143144178 scopus 로고    scopus 로고
    • Ketone-catalyzed asymmetric epoxidation reactions
    • (b) Yang, D. Ketone-catalyzed asymmetric epoxidation reactions. Acc. Chem. Res. 2004, 37, 497-505.
    • (2004) Acc. Chem. Res. , vol.37 , pp. 497-505
    • Yang, D.1
  • 21
    • 9944258961 scopus 로고    scopus 로고
    • Control of enantioselectivity by keto bile acid derivatives in the epoxidation of alkenes with oxone
    • (c) Bortolini, O.; Fantin, G.; Fogagnolo, Mari, L. Control of enantioselectivity by keto bile acid derivatives in the epoxidation of alkenes with oxone. Tetrahedron: Asymmetry 2004, 15, 3831-3833.
    • (2004) Tetrahedron: Asymmetry , vol.15 , pp. 3831-3833
    • Bortolini, O.1    Fantin, G.2    Fogagnolo3    Mari, L.4
  • 22
    • 30144437908 scopus 로고
    • Dioxiranes: Synthesis and reactions of methyldioxiranes
    • (a) Murray, R. W.; Jeyaraman, R. Dioxiranes: synthesis and reactions of methyldioxiranes. J. Org. Chem. 1985, 50, 2847-2853.
    • (1985) J. Org. Chem. , vol.50 , pp. 2847-2853
    • Murray, R.W.1    Jeyaraman, R.2
  • 23
    • 0001472942 scopus 로고
    • On the oxygen-17 and carbon-13 identification of the dimethyldioxirane intermediate arising in the reaction of potassium caroate with acetone
    • (b) Cassidei, L.; Fiorentino, M.; Mello, R.; Sciacovelli, O.; Curci, R. On the oxygen-17 and carbon-13 identification of the dimethyldioxirane intermediate arising in the reaction of potassium caroate with acetone. J. Org. Chem. 1987, 52, 699-700.
    • (1987) J. Org. Chem. , vol.52 , pp. 699-700
    • Cassidei, L.1    Fiorentino, M.2    Mello, R.3    Sciacovelli, O.4    Curci, R.5
  • 24
    • 0000598410 scopus 로고
    • On the isolation and characterization of methyl (trifluoromethyl) dioxirane
    • Mello, R.; Fiorentino, M.; Sciacovelli, O.; Curci, R. On the isolation and characterization of methyl (trifluoromethyl) dioxirane. J. Org. Chem. 1988, 53, 3890-3891.
    • (1988) J. Org. Chem. , vol.53 , pp. 3890-3891
    • Mello, R.1    Fiorentino, M.2    Sciacovelli, O.3    Curci, R.4
  • 25
    • 0030044090 scopus 로고    scopus 로고
    • On the triggering of free radical reactivity of dimethyldioxirane
    • Curci, R.; Dinoi, A.; Fusco, C.; Lillo, M. A. On the triggering of free radical reactivity of dimethyldioxirane. Tetrahedron Lett. 1996, 37, 249-252.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 249-252
    • Curci, R.1    Dinoi, A.2    Fusco, C.3    Lillo, M.A.4
  • 26
    • 0027234117 scopus 로고
    • Thermal decomposition of dimethyldioxirane
    • Hull, L. A.; Budhai, L. Thermal decomposition of dimethyldioxirane. Tetrahedron Lett. 1993, 34, 5039-5042.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5039-5042
    • Hull, L.A.1    Budhai, L.2
  • 27
    • 33344477827 scopus 로고    scopus 로고
    • Unpublished
    • Curci, R. Unpublished.
    • Curci, R.1
  • 28
    • 0043151043 scopus 로고    scopus 로고
    • Dioxirane epoxidations of alkenes
    • and references therein
    • Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Dioxirane epoxidations of alkenes. Org. React. 2002, 61, 219-515 and references therein.
    • (2002) Org. React. , vol.61 , pp. 219-515
    • Adam, W.1    Saha-Moller, C.R.2    Zhao, C.-G.3
  • 29
    • 33845183266 scopus 로고
    • Oxidations by methyl(trifluoromethyl)dioxirane. 2. Oxyfunctionalization of saturated hydrocarbons
    • (a) Mello, R.; Fiorentino, M.; Fusco, C.; Curci, R. Oxidations by methyl(trifluoromethyl)dioxirane. 2. Oxyfunctionalization of saturated hydrocarbons. J. Am. Chem. Soc. 1989, 111, 6749-6757.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6749-6757
    • Mello, R.1    Fiorentino, M.2    Fusco, C.3    Curci, R.4
  • 30
    • 0000963419 scopus 로고
    • Chemistry of dioxiranes. 4. Oxygen atom insertion into carbon-hydrogen bonds by dimethyldioxirane
    • (b) Murray, R. W.; Jeyaraman, R.; Mohan, L. Chemistry of dioxiranes. 4. Oxygen atom insertion into carbon-hydrogen bonds by dimethyldioxirane. J. Am. Chem. Soc. 1986, 108, 2470-2472.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 2470-2472
    • Murray, R.W.1    Jeyaraman, R.2    Mohan, L.3
  • 32
    • 0000553020 scopus 로고
    • Oxidations by methyl(trifluoromethyl)dioxirane. Conversion of alcohols into carbonyl compounds
    • Mello, R.; Cassidei, L.; Fiorentino, M.; Fusco, C.; Hümmer, W.; Jäger, V.; Curci, R. Oxidations by methyl(trifluoromethyl)dioxirane. Conversion of alcohols into carbonyl compounds. J. Am. Chem. Soc. 1991, 113, 2205-2208.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 2205-2208
    • Mello, R.1    Cassidei, L.2    Fiorentino, M.3    Fusco, C.4    Hümmer, W.5    Jäger, V.6    Curci, R.7
  • 33
    • 0028886460 scopus 로고
    • Mechanism of hydroxylation of alkanes by dimethyldioxirane. a radical-clock study
    • Vanni, R.; Garden, S. J.; Banks, J. T.; Ingold, K. U. Mechanism of hydroxylation of alkanes by dimethyldioxirane. A radical-clock study. Tetrahedron Lett. 1995, 36, 7999-8002.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7999-8002
    • Vanni, R.1    Garden, S.J.2    Banks, J.T.3    Ingold, K.U.4
  • 34
    • 0035479683 scopus 로고    scopus 로고
    • On the Hydroxylation of Bicyclo-[2.1.0]pentane using Dioxiranes
    • Curci, R.; D'Accolti, L.; Fusco, C. On the Hydroxylation of Bicyclo-[2.1.0]pentane using Dioxiranes. Tetrahedron Lett. 2001, 42, 7087-7090.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 7087-7090
    • Curci, R.1    D'Accolti, L.2    Fusco, C.3
  • 35
    • 0032487882 scopus 로고    scopus 로고
    • Dimethyldioxirane hydroxylation of a hypersensitive radical probe: Supporting evidence for an oxene insertion pathway
    • Simakov, P. A.; Choi, S.-Y.; Newcomb, M. Dimethyldioxirane hydroxylation of a hypersensitive radical probe: supporting evidence for an oxene insertion pathway. Tetrahedron Lett. 1998, 39, 8187-8190.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8187-8190
    • Simakov, P.A.1    Choi, S.-Y.2    Newcomb, M.3
  • 36
    • 0032517322 scopus 로고    scopus 로고
    • The nature of the transition structure for the oxidation of alkanes with dioxiranes
    • See also previous articles of the series quoted therein
    • Glukhovtsev, M. N.; Canepa, C.; Bach, R. D. The nature of the transition structure for the oxidation of alkanes with dioxiranes. J. Am. Chem. Soc. 1998, 120, 10528-10533. See also previous articles of the series quoted therein.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 10528-10533
    • Glukhovtsev, M.N.1    Canepa, C.2    Bach, R.D.3
  • 37
    • 0037423178 scopus 로고    scopus 로고
    • Novel pathways for oxygen insertion into unactivated C-H bonds by dioxiranes
    • (a) Freccero, M.; Gandolfi, R.; Sarzi-Amadé, M.; Rastelli, A. Novel pathways for oxygen insertion into unactivated C-H bonds by dioxiranes J. Org. Chem. 2003, 68, 811-823. (
    • (2003) J. Org. Chem. , vol.68
    • Freccero, M.1    Gandolfi, R.2    Sarzi-Amadé, M.3    Rastelli, A.4
  • 38
    • 0000845829 scopus 로고    scopus 로고
    • Transition states for alkane oxidations by dioxiranes
    • b) Du, X. H.; Houk, K. N. Transition states for alkane oxidations by dioxiranes. J. Org. Chem. 1998, 63, 6480-6483.
    • (1998) J. Org. Chem. , vol.63 , pp. 6480-6483
    • Du, X.H.1    Houk, K.N.2
  • 40
    • 0001107512 scopus 로고    scopus 로고
    • Mechanism of dioxirane oxidation of CH bonds
    • Shustov, G. V.; Rauk, A. Mechanism of dioxirane oxidation of CH bonds. J. Org. Chem. 1998, 63, 5413-5422.
    • (1998) J. Org. Chem. , vol.63 , pp. 5413-5422
    • Shustov, G.V.1    Rauk, A.2
  • 42
    • 0034692380 scopus 로고    scopus 로고
    • A model "rebound" mechanism of hydroxylation by cytochrome P450
    • and references therein
    • Ogliaro, F.; Harris, N.; Cohen, S.; Filatov, M.; de Visser, S. P.; Shaik, S. A model "rebound" mechanism of hydroxylation by cytochrome P450. J. Am. Chem. Soc. 2000, 122, 8977-8989 and references therein.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8977-8989
    • Ogliaro, F.1    Harris, N.2    Cohen, S.3    Filatov, M.4    De Visser, S.P.5    Shaik, S.6
  • 43
    • 33344461800 scopus 로고
    • Centropolyindans: Benzoannelated polyquinanes with a central carbon atom
    • Hargittai, I., Ed.; VCH: New York, Chapter 19
    • Kuck, D. Centropolyindans: benzoannelated polyquinanes with a central carbon atom. In Quasicrystals, networks, and molecules of fivefold symmetry; Hargittai, I., Ed.; VCH: New York, 1990; Chapter 19, pp 289-307.
    • (1990) Quasicrystals, Networks, and Molecules of Fivefold Symmetry , pp. 289-307
    • Kuck, D.1
  • 44
    • 0000467349 scopus 로고    scopus 로고
    • Oxyfunctionalization of nonnatural targets by dioxiranes. 2. Selective bridgehead hydroxylation of fenestrindane
    • See also previous article of the series
    • Fusco, C.; Fiorentino, M.; Dinoi, A.; Curci, R.; Krause, R. A.; Kuck, D. Oxyfunctionalization of nonnatural targets by dioxiranes. 2. Selective bridgehead hydroxylation of fenestrindane. J. Org. Chem. 1996, 61, 8681-8684. See also previous article of the series.
    • (1996) J. Org. Chem. , vol.61 , pp. 8681-8684
    • Fusco, C.1    Fiorentino, M.2    Dinoi, A.3    Curci, R.4    Krause, R.A.5    Kuck, D.6
  • 45
    • 84982503513 scopus 로고
    • Oxidation of cyclopropyl hydrocarbons with ozone
    • Proksch, E.; de Meijere, A. Oxidation of cyclopropyl hydrocarbons with ozone. Angew. Chem., Int. Ed. Engl. 1976, 15, 761-762.
    • (1976) Angew. Chem., Int. Ed. Engl. , vol.15 , pp. 761-762
    • Proksch, E.1    De Meijere, A.2
  • 46
    • 0141653998 scopus 로고    scopus 로고
    • Oxyfunctionalization of nonnatural targets by dioxiranes. 5. Selective oxidation of hydrocarbons bearing cyclopropyl moieties
    • D'Accolti, L.; Dinoi, A.; Fusco, C.; Russo, A.; Curci, R. Oxyfunctionalization of nonnatural targets by dioxiranes. 5. Selective oxidation of hydrocarbons bearing cyclopropyl moieties. J. Org. Chem. 2003, 68, 7806-7810.
    • (2003) J. Org. Chem. , vol.68 , pp. 7806-7810
    • D'Accolti, L.1    Dinoi, A.2    Fusco, C.3    Russo, A.4    Curci, R.5
  • 47
    • 0007705343 scopus 로고
    • Reactivity of geometrically constrained cyclopropylcarbinyl systems
    • For instance, see: Rhodes, Y. E.; DiFate, V. G. Reactivity of geometrically constrained cyclopropylcarbinyl systems. J. Am. Chem. Soc. 1972, 94, 7582-7583.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 7582-7583
    • Rhodes, Y.E.1    DiFate, V.G.2
  • 48
    • 0000856855 scopus 로고
    • Oxidation of 2,4-didehydroadamantane
    • Teager, D. S.; Murray, R. K., Jr. Oxidation of 2,4-didehydroadamantane. J. Org. Chem. 1993, 58, 5548-5550.
    • (1993) J. Org. Chem. , vol.58 , pp. 5548-5550
    • Teager, D.S.1    Murray Jr., R.K.2
  • 49
    • 0037140738 scopus 로고    scopus 로고
    • Revisiting the mechanism of P450 enzymes with the radical clocks norcarane and spiro[2,5]octane
    • Auclair, K.; Hu, Z.; Little, D. M.; Ortiz de Montellano, P. R.; Groves, J. T. Revisiting the mechanism of P450 enzymes with the radical clocks norcarane and spiro[2,5]octane. J. Am. Chem. Soc. 2002, 124, 6020-6027.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6020-6027
    • Auclair, K.1    Hu, Z.2    Little, D.M.3    Ortiz De Montellano, P.R.4    Groves, J.T.5
  • 50
    • 0035966175 scopus 로고    scopus 로고
    • Oxyfunctionalization of nonnatural targets by dioxiranes. 4. Efficient oxidation of binor S using methyl(trifluoromethyl)-dioxirane
    • D'Accolti, L.; Fusco, C.; Lucchini, V.; Carpenter, G. B.; Curci, R. Oxyfunctionalization of nonnatural targets by dioxiranes. 4. Efficient oxidation of binor S using methyl(trifluoromethyl)-dioxirane. J. Org. Chem. 2001, 66, 9063-9066.
    • (2001) J. Org. Chem. , vol.66 , pp. 9063-9066
    • D'Accolti, L.1    Fusco, C.2    Lucchini, V.3    Carpenter, G.B.4    Curci, R.5
  • 51
    • 0007615225 scopus 로고
    • Regiospecific oxidation of binor S and acid-catalyzed rearrangement of the product
    • Pramod, K.; Eaton, P. E.; Gilardi, R.; Flippen-Anderson, J. L. Regiospecific oxidation of binor S and acid-catalyzed rearrangement of the product. J. Org. Chem. 1990, 55, 6105-6107.
    • (1990) J. Org. Chem. , vol.55 , pp. 6105-6107
    • Pramod, K.1    Eaton, P.E.2    Gilardi, R.3    Flippen-Anderson, J.L.4
  • 52
    • 0037189113 scopus 로고    scopus 로고
    • Chemo-and regioselective oxidation of adamantly derivatives by dioxiranes
    • (a) D'Accolti, L.; Kang, P.; Khan, S.; Curci, R.; Foote, C. S. Chemo-and regioselective oxidation of adamantly derivatives by dioxiranes. Tetrahedron Lett. 2002, 43, 4649-4652.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4649-4652
    • D'Accolti, L.1    Kang, P.2    Khan, S.3    Curci, R.4    Foote, C.S.5
  • 53
    • 0042684887 scopus 로고    scopus 로고
    • Hyperconjugative control by remote substituents of diastereoselectivity in the oxygenation of hydrocarbons
    • (b) Gonzalès-Nuñez, M. E.; Royo, J.; Castellano, G.; Andreu, C.; Boix, C.; Mello, R. Asensio, G. Hyperconjugative control by remote substituents of diastereoselectivity in the oxygenation of hydrocarbons. Org. Lett. 2000, 2, 831-834.
    • (2000) Org. Lett. , vol.2 , pp. 831-834
    • Gonzalès-Nuñez, M.E.1    Royo, J.2    Castellano, G.3    Andreu, C.4    Boix, C.5    Mello, R.6    Asensio, G.7
  • 54
    • 0043032782 scopus 로고    scopus 로고
    • Investigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in situ
    • (c) Wong, M.-K.; Chung, N.-W.; He, L.; Wang, X.-C.; Van, Z.; Tang, Y.-C.; Yang, D. Investigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in situ. J. Org. Chem. 2003, 68, 6321-6328.
    • (2003) J. Org. Chem. , vol.68 , pp. 6321-6328
    • Wong, M.-K.1    Chung, N.-W.2    He, L.3    Wang, X.-C.4    Van, Z.5    Tang, Y.-C.6    Yang, D.7
  • 55
    • 0000458209 scopus 로고
    • Substrate-directable chemical reactions
    • and references therein
    • For instance, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Substrate-directable chemical reactions. Chem. Rev. 1993, 93, 1307-1370 and references therein.
    • (1993) Chem. Rev. , vol.93 , pp. 1307-1370
    • Hoveyda, A.H.1    Evans, D.A.2    Fu, G.C.3
  • 56
    • 0037178337 scopus 로고    scopus 로고
    • Catalytic oxidations of steroid substrates by artificial cytochrome P-450 enzymes
    • Yang, J.; Gabriele, B.; Belvedere, S.; Huang, Y.; Breslow, R. Catalytic oxidations of steroid substrates by artificial cytochrome P-450 enzymes. J. Org. Chem. 2002, 67, 5057-5067.
    • (2002) J. Org. Chem. , vol.67 , pp. 5057-5067
    • Yang, J.1    Gabriele, B.2    Belvedere, S.3    Huang, Y.4    Breslow, R.5
  • 57
    • 0000050003 scopus 로고
    • Oxidation of natural targets by dioxiranes. Oxyfunctionalization of steroids
    • (a) Bovicelli, P.; Lupattelli, P.; Mincione, E.; Prencipe, T.; Curci, R. Oxidation of natural targets by dioxiranes. Oxyfunctionalization of steroids. J. Org. Chem. 1992, 57, 2182-2184.
    • (1992) J. Org. Chem. , vol.57 , pp. 2182-2184
    • Bovicelli, P.1    Lupattelli, P.2    Mincione, E.3    Prencipe, T.4    Curci, R.5
  • 58
    • 0026644850 scopus 로고
    • Oxidation of natural targets by dioxiranes. 2. Direct hydroxylation at the side chain C-25 of cholestane derivatives and of Windaus-Grundmann ketone
    • (b) Bovicelli, P.; Lupattelli, P.; Mincione, E.; Prencipe, T.; Curci, R. Oxidation of natural targets by dioxiranes. 2. Direct hydroxylation at the side chain C-25 of cholestane derivatives and of Windaus-Grundmann ketone. J. Org. Chem. 1992, 57, 5052-5054.
    • (1992) J. Org. Chem. , vol.57 , pp. 5052-5054
    • Bovicelli, P.1    Lupattelli, P.2    Mincione, E.3    Prencipe, T.4    Curci, R.5
  • 59
    • 0029862761 scopus 로고    scopus 로고
    • 2 to its (all-R) tetraepoxide and C-25 hydroxy derivative
    • See also previous articles of this series
    • 2 to its (all-R) tetraepoxide and C-25 hydroxy derivative. J. Am. Chem. Soc. 1996, 118, 11089-11092. See also previous articles of this series.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11089-11092
    • Curci, R.1    Detomaso, A.2    Lattanzio, M.E.3    Carpenter, G.B.4
  • 61
    • 0141629765 scopus 로고    scopus 로고
    • New oxidative tools for the functionalization of the cephalostatin north 1 hemisphere
    • Lee, J. S.; Fuchs, P. L. New oxidative tools for the functionalization of the cephalostatin north 1 hemisphere. Org. Lett. 2003, 5, 2247-2250.
    • (2003) Org. Lett. , vol.5 , pp. 2247-2250
    • Lee, J.S.1    Fuchs, P.L.2
  • 63
    • 0001474702 scopus 로고
    • Regioselective oxyfunctionalization of unactivated tertiary and secondary carbon-hydrogen bonds of alkylamines by methyl(trifluoromethyl)dioxirane in acid medium
    • Asensio, G.; Gonzalès-Nuñez, M. E.; Bernardini, C. B.; Mello, R.; Adam, W. Regioselective oxyfunctionalization of unactivated tertiary and secondary carbon-hydrogen bonds of alkylamines by methyl(trifluoromethyl) dioxirane in acid medium. J. Am. Chem. Soc. 1993, 115, 7250-7253.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 7250-7253
    • Asensio, G.1    Gonzalès-Nuñez, M.E.2    Bernardini, C.B.3    Mello, R.4    Adam, W.5
  • 64
    • 0033550173 scopus 로고    scopus 로고
    • A new and efficient synthesis of unnatural amino acids and peptides by selective 3,3-dimethyldioxirane side-chain oxidation
    • Saladino, R.; Mezzetti, M.; Mincione, E.; Torrini, I.; Paglialunga Paradisi, M.; Mastropietro, G. A new and efficient synthesis of unnatural amino acids and peptides by selective 3,3-dimethyldioxirane side-chain oxidation. J. Org. Chem. 1999, 64, 8468-8474.
    • (1999) J. Org. Chem. , vol.64 , pp. 8468-8474
    • Saladino, R.1    Mezzetti, M.2    Mincione, E.3    Torrini, I.4    Paglialunga Paradisi, M.5    Mastropietro, G.6
  • 65
    • 0035931408 scopus 로고    scopus 로고
    • Oxidation of natural targets by dioxiranes. Part 4: A novel approach to the synthesis of N-hydroxyamino acids using dioxiranes
    • Detomaso, A.; Curci, R. Oxidation of natural targets by dioxiranes. Part 4: A novel approach to the synthesis of N-hydroxyamino acids using dioxiranes. Tetrahedron Lett. 2001, 42, 755-758.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 755-758
    • Detomaso, A.1    Curci, R.2
  • 66
    • 0032584442 scopus 로고    scopus 로고
    • Decomposition modes of dioxirane, methyldioxirane and dimethyldioxirane
    • Cremer, D.; Kraka, E.; Szalay, P. G. Decomposition modes of dioxirane, methyldioxirane and dimethyldioxirane. Chem. Phys. Lett. 1998, 292, 97-109.
    • (1998) Chem. Phys. Lett. , vol.292 , pp. 97-109
    • Cremer, D.1    Kraka, E.2    Szalay, P.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.