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Volumn 54, Issue 22, 1989, Pages 5292-5302

Ruthenium(II)-Catalyzed Reactions of 1,4-Epiperoxides

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EID: 0001459493     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00283a023     Document Type: Article
Times cited : (72)

References (65)
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    • For the catalysis with metals other than Fe, see: (a) [Cu(I) and Cu(II)] (b) [Ti(III)] Paget, H. J. Chem. Soc. 1938, 829. See also ref 4b. (c) [V(IV)], ref 4e. (d) [Pb(IV)] Schenck, G. O. Angew. Chem. 1952, 64, 12. (e) [Sn(II)] Natsume, H.; Muratake, H. Tetrahedron Lett. 1979, 3477, and references therein. (f) [Co(II)] Boyd, J. D.; Foote, C. S.; Imagawa, D. K. J. Am. Chem. Soc. 1980, 102, 3641. Sutbeyaz, Y.; Secen, H.; Balci, M. J. Org. Chem. 1988, 53, 2312. (g) Balci, M.; Aklbulut, N. Tetrahedron 1985, 41, (h) [Rh(I)] Hagenbach, J. P.; Vogel, P. J. Chem. Soc., Chem. Commun. 1980, 1062; Hagenbach, J. P.; Birbaum, J. L.; Metral, J. L.; Vogel, P. Helv. Chim. Acta 1982, 65, 887. (i) [Pd(0)] Suzuki, M.; Noyori, R.; Hamanaka, N. J. Am. Chem. Soc. 1981, 103, 5606. Suzuki, M.; Oda, Y. Noyori, R. Tetrahedron Lett. 1981, 22, 4413.
    • For the catalysis with metals other than Fe, see: (a) [Cu(I) and Cu(II)] Porter, N. A.; Nixon, J. R.; Gilmore, D. W. ACS Symp. Ser. 1978, No. 69, 89. (b) [Ti(III)] Paget, H. J. Chem. Soc. 1938, 829. See also ref 4b. (c) [V(IV)], ref 4e. (d) [Pb(IV)] Schenck, G. O. Angew. Chem. 1952, 64, 12. (e) [Sn(II)] Natsume, H.; Muratake, H. Tetrahedron Lett. 1979, 3477, and references therein. (f) [Co(II)] Boyd, J. D.; Foote, C. S.; Imagawa, D. K. J. Am. Chem. Soc. 1980, 102, 3641. Sutbeyaz, Y.; Secen, H.; Balci, M. J. Org. Chem. 1988, 53, 2312. (g) Balci, M.; Aklbulut, N. Tetrahedron 1985, 41, (h) [Rh(I)] Hagenbach, J. P.; Vogel, P. J. Chem. Soc., Chem. Commun. 1980, 1062; Hagenbach, J. P.; Birbaum, J. L.; Metral, J. L.; Vogel, P. Helv. Chim. Acta 1982, 65, 887. (i) [Pd(0)] Suzuki, M.; Noyori, R.; Hamanaka, N. J. Am. Chem. Soc. 1981, 103, 5606. Suzuki, M.; Oda, Y. Noyori, R. Tetrahedron Lett. 1981, 22, 4413.
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    • and references therein. For the acid-catalyzed cleavage, see: Yoshida, M.; Miura, M.; Kusabayashi, S. J. Am. Chem. Soc. 1983, 105, 6279; Jefford, C. W.; Jaggi, D.; Boukouvalas, J.; Kohmoto, S. 1983, 105, 6497; Jefford, C. W.; Rossier, J. C.; Kohmoto, S.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1984. 1496.
    • Carless, H. A. J.; Atkins, R.; Fekarurhobo, G. K. Tetrahedron Lett. 1985, 26, 803, and references therein. For the acid-catalyzed cleavage, see: Yoshida, M.; Miura, M.; Kusabayashi, S. J. Am. Chem. Soc. 1983, 105, 6279; Jefford, C. W.; Jaggi, D.; Boukouvalas, J.; Kohmoto, S. 1983, 105, 6497; Jefford, C. W.; Rossier, J. C.; Kohmoto, S.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1984. 1496.
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    • (b) Porter, N. A. In Free Radicals In Biology; Pryor, W. A., Ed.; Academic Press: New York, 1980; Vol. IV, Chapter 8. (c) Hermann, G.; Ruf, H. H.; Ullrich, V. Angew. Chem., Int. Ed. Engl. 1983, 22, 487. (d) Takahashi, K.; Kishi, M. J. Chem. Soc., Chem. Commun. 1987, 722. (e) Tetrahedron Lett. 1988, 29, 4595.
    • Turner, J. A.; Herz, W. Experientia 1977, 33, 1133. (b) Porter, N. A. In Free Radicals In Biology; Pryor, W. A., Ed.; Academic Press: New York, 1980; Vol. IV, Chapter 8. (c) Hermann, G.; Ruf, H. H.; Ullrich, V. Angew. Chem., Int. Ed. Engl. 1983, 22, 487. (d) Takahashi, K.; Kishi, M. J. Chem. Soc., Chem. Commun. 1987, 722. (e) Tetrahedron Lett. 1988, 29, 4595.
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    • For the chemical models other than the reaction with Fe(II) salts, see ref 5i and:. 1982, 104, 3498;. 1984, 106, 1750. Salomon, R. G.; Miller, D. B.; Zagorski, M. G.; Coughlin, D. J. 1984, 106, 6049. Wilson, R. M.; Schnaap, K. A.; Merwin, R. K.; Ranganathan, R.; Moats, D. L.; Conrad, T. T. J. Org. Chem. 1986, 51, 4028. (9) Ru(II)-porphyrin complexes are known to mimic heme proteins: Farrell, N.; Dolphin, D. H.; James, B. R. J. Am. Chem. Soc. 1978, 100, 324.
    • For the chemical models other than the reaction with Fe(II) salts, see ref 5i and: Zagorski, M. G.; Salomon, R. G. J. Am. Chem. Soc. 1980, 102, 2501;. 1982, 104, 3498;. 1984, 106, 1750. Salomon, R. G.; Miller, D. B.; Zagorski, M. G.; Coughlin, D. J. 1984, 106, 6049. Wilson, R. M.; Schnaap, K. A.; Merwin, R. K.; Ranganathan, R.; Moats, D. L.; Conrad, T. T. J. Org. Chem. 1986, 51, 4028. (9) Ru(II)-porphyrin complexes are known to mimic heme proteins: Farrell, N.; Dolphin, D. H.; James, B. R. J. Am. Chem. Soc. 1978, 100, 324.
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    • and references therein. See also a review: Jardine, F. H. In Progress in Inorganic Chemistry; Lippard, S. J., Ed.; Wiley: New York, 1984; Vol. 31, pp 265–370.
    • Matsumoto, H.; Nakano, T.; Takatsu, K. Nagai, Y. J. Org. Chem. 1978, 43, 1734, and references therein. See also a review: Jardine, F. H. In Progress in Inorganic Chemistry; Lippard, S. J., Ed.; Wiley: New York, 1984; Vol. 31, pp 265–370.
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    • Preliminary reports
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    • Preliminary reports: Suzuki, M.; Noyori, R.; Hamanaka, N. J. Am. Chem. Soc. 1982, 104, 2024; Noyori, R.; Suzuki, M. Angew. Chem., Int. Ed. Engl. 1984, 23, 847.
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    • For thermolysis of 1, see (a) Couglin, D. J.; Salomon, R. G. J. Am. Chem. Soc. 1979, 101, 2761. (b) Bloodworth, A. J.; Baker, D. S. J. Chem. Soc., Chem. Commun. 1981, 547. For thermolysis of 2, see (c) Moore, C. G. J. Chem. Soc. 1951, 254. For CoIITPP-catalyzed decomposition of bicyclic saturated 1,4-epiperoxides, see ref 5g.
    • Salomon, R. G.; Salomon, M. F.; Coughlin, D. J. J. Am. Chem. Soc. 1978, 100, 660. For thermolysis of 1, see (a) Couglin, D. J.; Salomon, R. G. J. Am. Chem. Soc. 1979, 101, 2761. (b) Bloodworth, A. J.; Baker, D. S. J. Chem. Soc., Chem. Commun. 1981, 547. For thermolysis of 2, see (c) Moore, C. G. J. Chem. Soc. 1951, 254. For CoIITPP-catalyzed decomposition of bicyclic saturated 1,4-epiperoxides, see ref 5g.
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    • Treatment
    • Treatment of PGH2 with FeCl2in aqueous solution was claimed to give (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid in 40-50% yield without any definite stereochemical evidence.44
    • , vol.8 , Issue.10 , pp. 40-50
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    • Thermodynamic ratio of (E, E)-, (E, Z)-, and (Z, Z)-2,4-hexadiene is 65.5:30.7:3.8 at 20.2 °C
    • Thermodynamic ratio of (E, E)-, (E, Z)-, and (Z, Z)-2,4-hexadiene is 65.5:30.7:3.8 at 20.2 °C: Doring, C. E.; Hauthal, H. G. J. Prakt. Chem. 1964, 24, 27.
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    • Advances in Prostaglandin and
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    • For biosynthetic production of HHT from PGG2 or PGH2, see: Nugteren, D. H.; Christ-Hazelhof, E. In Advances in Prostaglandin and Thromboxane Research; Samuelsson, B., Ramwell, P. W., Paoletti, R., Eds.; Raven Press: New York, 1980; pp 129–137. Haurand, M.; Ullrich, V. J. Biol. Chem. 1985, 260, 15059.
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    • For reasonable threo/erythro nomenclature, see
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    • For reasonable threo/erythro nomenclature, see: Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106. Noyori, R.; Nishida, I.; Sakata, J.; Nishizawa, M. 1983, 105, 1598.
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    • The phosphine does react with cyclic peroxides; reaction with saturated epiperoxides produces the diols, whereas reaction with 2,3-unsaturated 1,4-epiperoxides affords 1,3-diene 1,2-epoxides: see However, under the present catalytic conditions, it does not participate in the product formation to any great extent.
    • The phosphine does react with cyclic peroxides; reaction with saturated epiperoxides produces the diols, whereas reaction with 2,3-unsaturated 1,4-epiperoxides affords 1,3-diene 1,2-epoxides: see Clennan, E. L.; Heah, P. C. J. Org. Chem. 1981, 46, 4105. However, under the present catalytic conditions, it does not participate in the product formation to any great extent.
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    • The C(5)-C(6) double bond could also stabilize the transition state via homoallylic conjugation. See
    • The C(5)-C(6) double bond could also stabilize the transition state via homoallylic conjugation. See: Ingold, K. U. ACS Symp. Ser. 1978, No. 69, 187.
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    • (b) Coughlin, D. J.; Brown, R. S.; Salomon, R. G. J. Am. Chem. Soc. 1979, 101, 1533.
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    • (b) Kondo, T.; Tanimoto, M.; Matsumoto, M. 1980, 21, 1649.
    • Kondo, T.; Matsumoto, M.; Tanimoto, M. Tetrahedron Lett. 1978, 3819. (b) Kondo, T.; Tanimoto, M.; Matsumoto, M. 1980, 21, 1649.
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    • The same
    • The same conclusion was obtained for the epiperoxides 20 (-110 °C, CD2C12), 22 (-126 °C, CD2C12), 23 (-124 °C, CD2C12), and 25 (-100 °C, CD2C12), respectively (see Experimental Section).
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    • Application of this Ru(II)-catalyzed reaction: (synthesis of chorismic acid): Decomposition of trioxides: Ito, Y.; Matsuura, A.; Otani, R.; Matsuura, T. 1983, 105, 5699. Matsuura, A.; Nishinaga, A.; Ito, Y.; Matsuura, T. Chem. Lett. 1985, 993.
    • Application of this Ru(II)-catalyzed reaction: (synthesis of chorismic acid): Hoare, J. H.; Policastro, P. P.; Berchtold, G. A. J. Am. Chem. Soc. 1983, 105, 6264. Decomposition of trioxides: Ito, Y.; Matsuura, A.; Otani, R.; Matsuura, T. 1983, 105, 5699. Matsuura, A.; Nishinaga, A.; Ito, Y.; Matsuura, T. Chem. Lett. 1985, 993.
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    • See also: Porter, N. A.; Byers, J. D.; Ali, A. E.; Eling, T. E. J. Am. Chem. Soc. 1980, 102, 1183.
    • Porter, N. A.; Byers, J. D.; Mebane, R. C.; Gilmore, D. W.; Nixon, J. R. J. Org. Chem. 1978, 43, 2088. See also: Porter, N. A.; Byers, J. D.; Ali, A. E.; Eling, T. E. J. Am. Chem. Soc. 1980, 102, 1183.
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    • Kondo, K.; Matsumoto, M. J. Chem. Soc., Chem. Commun. 1972, 1332. Matsumoto, M.; Dobashi, S.; Kuroda, K.; Kondo, K. Tetrahedron 1985, 41. 2147.
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    • Similar phenomena were observed in photooxygenation of (E,-Z)-2,4-hexadiene. See
    • Similar phenomena were observed in photooxygenation of (E,-Z)-2,4-hexadiene. See: Gollnick, K.; Griesbeck, A. Tetrahedron Lett. 1983, 24, 3303.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 3303
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