메뉴 건너뛰기




Volumn , Issue 21, 2002, Pages 2570-2571

High-valent metalloporphyrin, Fe(tpp)OTf, catalyzed rearrangement of α,β-epoxy ketones into 1,2-diketones

Author keywords

[No Author keywords available]

Indexed keywords

IRON COMPLEX; KETONE DERIVATIVE; LEWIS ACID; METALLOPORPHYRIN;

EID: 0036979998     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b207328e     Document Type: Article
Times cited : (96)

References (33)
  • 2
    • 0013025463 scopus 로고
    • H. O. House, J. Am. Chem. Soc., 1954, 76, 1235; H. O. House and G. D. Ryerson, J. Am. Chem. Soc., 1961, 83, 979 and references cited therein.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 1235
    • House, H.O.1
  • 3
    • 0001647124 scopus 로고
    • and references cited therein
    • H. O. House, J. Am. Chem. Soc., 1954, 76, 1235; H. O. House and G. D. Ryerson, J. Am. Chem. Soc., 1961, 83, 979 and references cited therein.
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 979
    • House, H.O.1    Ryerson, G.D.2
  • 4
    • 0012939455 scopus 로고
    • R. D. Bach and J. M. Domagala, J. Org. Chem., 1984, 49, 4181; R. D. Bach and R. C. Klix, J. Org. Chem., 1985, 50, 5440; F. Kunisch, K. Horbert and P. Welzel, Tetrahedron Lett., 1985, 26, 6039; R. D. Bach and R. C. Klix, Tetrahedron Lett., 1985, 26, 985; R. C. Klix and R. D. Bach, J. Org. Chem., 1987, 52, 580; K. Okada, T. Katsura, H. Tanino, H. Kakoi and S. Inoue, Chem. Lett., 1994, 157; S. Sankararaman and J. E. Nesakumar, J. Chem. Soc., Perkin Trans. 1, 1999, 3173; J. A. Elings, H. E. B. Lempers and R. A. Sheldon, Eur. J. Org. Chem., 2000, 1950.
    • (1984) J. Org. Chem. , vol.49 , pp. 4181
    • Bach, R.D.1    Domagala, J.M.2
  • 5
    • 0012981088 scopus 로고
    • R. D. Bach and J. M. Domagala, J. Org. Chem., 1984, 49, 4181; R. D. Bach and R. C. Klix, J. Org. Chem., 1985, 50, 5440; F. Kunisch, K. Horbert and P. Welzel, Tetrahedron Lett., 1985, 26, 6039; R. D. Bach and R. C. Klix, Tetrahedron Lett., 1985, 26, 985; R. C. Klix and R. D. Bach, J. Org. Chem., 1987, 52, 580; K. Okada, T. Katsura, H. Tanino, H. Kakoi and S. Inoue, Chem. Lett., 1994, 157; S. Sankararaman and J. E. Nesakumar, J. Chem. Soc., Perkin Trans. 1, 1999, 3173; J. A. Elings, H. E. B. Lempers and R. A. Sheldon, Eur. J. Org. Chem., 2000, 1950.
    • (1985) J. Org. Chem. , vol.50 , pp. 5440
    • Bach, R.D.1    Klix, R.C.2
  • 6
    • 0001649704 scopus 로고
    • R. D. Bach and J. M. Domagala, J. Org. Chem., 1984, 49, 4181; R. D. Bach and R. C. Klix, J. Org. Chem., 1985, 50, 5440; F. Kunisch, K. Horbert and P. Welzel, Tetrahedron Lett., 1985, 26, 6039; R. D. Bach and R. C. Klix, Tetrahedron Lett., 1985, 26, 985; R. C. Klix and R. D. Bach, J. Org. Chem., 1987, 52, 580; K. Okada, T. Katsura, H. Tanino, H. Kakoi and S. Inoue, Chem. Lett., 1994, 157; S. Sankararaman and J. E. Nesakumar, J. Chem. Soc., Perkin Trans. 1, 1999, 3173; J. A. Elings, H. E. B. Lempers and R. A. Sheldon, Eur. J. Org. Chem., 2000, 1950.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 6039
    • Kunisch, F.1    Horbert, K.2    Welzel, P.3
  • 7
    • 13344296403 scopus 로고
    • R. D. Bach and J. M. Domagala, J. Org. Chem., 1984, 49, 4181; R. D. Bach and R. C. Klix, J. Org. Chem., 1985, 50, 5440; F. Kunisch, K. Horbert and P. Welzel, Tetrahedron Lett., 1985, 26, 6039; R. D. Bach and R. C. Klix, Tetrahedron Lett., 1985, 26, 985; R. C. Klix and R. D. Bach, J. Org. Chem., 1987, 52, 580; K. Okada, T. Katsura, H. Tanino, H. Kakoi and S. Inoue, Chem. Lett., 1994, 157; S. Sankararaman and J. E. Nesakumar, J. Chem. Soc., Perkin Trans. 1, 1999, 3173; J. A. Elings, H. E. B. Lempers and R. A. Sheldon, Eur. J. Org. Chem., 2000, 1950.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 985
    • Bach, R.D.1    Klix, R.C.2
  • 8
    • 33845281348 scopus 로고
    • R. D. Bach and J. M. Domagala, J. Org. Chem., 1984, 49, 4181; R. D. Bach and R. C. Klix, J. Org. Chem., 1985, 50, 5440; F. Kunisch, K. Horbert and P. Welzel, Tetrahedron Lett., 1985, 26, 6039; R. D. Bach and R. C. Klix, Tetrahedron Lett., 1985, 26, 985; R. C. Klix and R. D. Bach, J. Org. Chem., 1987, 52, 580; K. Okada, T. Katsura, H. Tanino, H. Kakoi and S. Inoue, Chem. Lett., 1994, 157; S. Sankararaman and J. E. Nesakumar, J. Chem. Soc., Perkin Trans. 1, 1999, 3173; J. A. Elings, H. E. B. Lempers and R. A. Sheldon, Eur. J. Org. Chem., 2000, 1950.
    • (1987) J. Org. Chem. , vol.52 , pp. 580
    • Klix, R.C.1    Bach, R.D.2
  • 9
    • 0002447983 scopus 로고
    • R. D. Bach and J. M. Domagala, J. Org. Chem., 1984, 49, 4181; R. D. Bach and R. C. Klix, J. Org. Chem., 1985, 50, 5440; F. Kunisch, K. Horbert and P. Welzel, Tetrahedron Lett., 1985, 26, 6039; R. D. Bach and R. C. Klix, Tetrahedron Lett., 1985, 26, 985; R. C. Klix and R. D. Bach, J. Org. Chem., 1987, 52, 580; K. Okada, T. Katsura, H. Tanino, H. Kakoi and S. Inoue, Chem. Lett., 1994, 157; S. Sankararaman and J. E. Nesakumar, J. Chem. Soc., Perkin Trans. 1, 1999, 3173; J. A. Elings, H. E. B. Lempers and R. A. Sheldon, Eur. J. Org. Chem., 2000, 1950.
    • (1994) Chem. Lett. , pp. 157
    • Okada, K.1    Katsura, T.2    Tanino, H.3    Kakoi, H.4    Inoue, S.5
  • 10
    • 0000398414 scopus 로고    scopus 로고
    • R. D. Bach and J. M. Domagala, J. Org. Chem., 1984, 49, 4181; R. D. Bach and R. C. Klix, J. Org. Chem., 1985, 50, 5440; F. Kunisch, K. Horbert and P. Welzel, Tetrahedron Lett., 1985, 26, 6039; R. D. Bach and R. C. Klix, Tetrahedron Lett., 1985, 26, 985; R. C. Klix and R. D. Bach, J. Org. Chem., 1987, 52, 580; K. Okada, T. Katsura, H. Tanino, H. Kakoi and S. Inoue, Chem. Lett., 1994, 157; S. Sankararaman and J. E. Nesakumar, J. Chem. Soc., Perkin Trans. 1, 1999, 3173; J. A. Elings, H. E. B. Lempers and R. A. Sheldon, Eur. J. Org. Chem., 2000, 1950.
    • (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 3173
    • Sankararaman, S.1    Nesakumar, J.E.2
  • 11
    • 0012989812 scopus 로고    scopus 로고
    • R. D. Bach and J. M. Domagala, J. Org. Chem., 1984, 49, 4181; R. D. Bach and R. C. Klix, J. Org. Chem., 1985, 50, 5440; F. Kunisch, K. Horbert and P. Welzel, Tetrahedron Lett., 1985, 26, 6039; R. D. Bach and R. C. Klix, Tetrahedron Lett., 1985, 26, 985; R. C. Klix and R. D. Bach, J. Org. Chem., 1987, 52, 580; K. Okada, T. Katsura, H. Tanino, H. Kakoi and S. Inoue, Chem. Lett., 1994, 157; S. Sankararaman and J. E. Nesakumar, J. Chem. Soc., Perkin Trans. 1, 1999, 3173; J. A. Elings, H. E. B. Lempers and R. A. Sheldon, Eur. J. Org. Chem., 2000, 1950.
    • (2000) Eur. J. Org. Chem. , pp. 1950
    • Elings, J.A.1    Lempers, H.E.B.2    Sheldon, R.A.3
  • 12
    • 0000993412 scopus 로고
    • Photo irradiation and a Pd(0) catalyst are also effective for the selective rearrangement of epoxy ketones into 1,3-diketones: S. P. Pappas, R. M. Gresham and M. J. Miller, J. Am. Chem. Soc., 1970, 92, 5797; M. Suzuki, A. Watanabe and R. Noyori, J. Am. Chem. Soc., 1980, 102, 2095.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 5797
    • Pappas, S.P.1    Gresham, R.M.2    Miller, M.J.3
  • 13
    • 0000780620 scopus 로고
    • Photo irradiation and a Pd(0) catalyst are also effective for the selective rearrangement of epoxy ketones into 1,3-diketones: S. P. Pappas, R. M. Gresham and M. J. Miller, J. Am. Chem. Soc., 1970, 92, 5797; M. Suzuki, A. Watanabe and R. Noyori, J. Am. Chem. Soc., 1980, 102, 2095.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 2095
    • Suzuki, M.1    Watanabe, A.2    Noyori, R.3
  • 14
    • 0030815127 scopus 로고    scopus 로고
    • K. Okada, K. Murakami and H. Tanino, Tetrahedron, 1997, 53, 14247; K. Okada, K. Murakami, H. Tanino, H. Kakoi and S. Inoue, Heterocycles, 1996, 43, 1735; M. Asaoka, S. Hayashibe, S. Sonoda and H. Takei, Tetrahedron, 1991, 47, 6967; V. Enev and E. Tsankova, Tetrahedron Lett., 1988, 29, 1829.
    • (1997) Tetrahedron , vol.53 , pp. 14247
    • Okada, K.1    Murakami, K.2    Tanino, H.3
  • 15
    • 0001577212 scopus 로고    scopus 로고
    • K. Okada, K. Murakami and H. Tanino, Tetrahedron, 1997, 53, 14247; K. Okada, K. Murakami, H. Tanino, H. Kakoi and S. Inoue, Heterocycles, 1996, 43, 1735; M. Asaoka, S. Hayashibe, S. Sonoda and H. Takei, Tetrahedron, 1991, 47, 6967; V. Enev and E. Tsankova, Tetrahedron Lett., 1988, 29, 1829.
    • (1996) Heterocycles , vol.43 , pp. 1735
    • Okada, K.1    Murakami, K.2    Tanino, H.3    Kakoi, H.4    Inoue, S.5
  • 16
    • 0025738036 scopus 로고
    • K. Okada, K. Murakami and H. Tanino, Tetrahedron, 1997, 53, 14247; K. Okada, K. Murakami, H. Tanino, H. Kakoi and S. Inoue, Heterocycles, 1996, 43, 1735; M. Asaoka, S. Hayashibe, S. Sonoda and H. Takei, Tetrahedron, 1991, 47, 6967; V. Enev and E. Tsankova, Tetrahedron Lett., 1988, 29, 1829.
    • (1991) Tetrahedron , vol.47 , pp. 6967
    • Asaoka, M.1    Hayashibe, S.2    Sonoda, S.3    Takei, H.4
  • 17
    • 0001101387 scopus 로고
    • K. Okada, K. Murakami and H. Tanino, Tetrahedron, 1997, 53, 14247; K. Okada, K. Murakami, H. Tanino, H. Kakoi and S. Inoue, Heterocycles, 1996, 43, 1735; M. Asaoka, S. Hayashibe, S. Sonoda and H. Takei, Tetrahedron, 1991, 47, 6967; V. Enev and E. Tsankova, Tetrahedron Lett., 1988, 29, 1829.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 1829
    • Enev, V.1    Tsankova, E.2
  • 18
    • 0027180575 scopus 로고
    • 3 mediated rearrangements of chalcone epoxides into 1,3-diarylpropane-1,2-diones have been reported, the substrates exemplified in these reports are strictly restricted to chalcone epoxide derivatives: (a) T. B. Rao and J. M. Rao, Synth. Commun., 1993, 23, 1527; (b) O. N. Bubel, I. G. Tishchenko and O. A. Grinkevich, Khim. Geterotsikl. Soedin., 1985, 1624.
    • (1993) Synth. Commun. , vol.23 , pp. 1527
    • Rao, T.B.1    Rao, J.M.2
  • 19
    • 24544440736 scopus 로고
    • 3 mediated rearrangements of chalcone epoxides into 1,3-diarylpropane-1,2-diones have been reported, the substrates exemplified in these reports are strictly restricted to chalcone epoxide derivatives: (a) T. B. Rao and J. M. Rao, Synth. Commun., 1993, 23, 1527; O. N. Bubel, I. G. Tishchenko and O. A. Grinkevich, Khim. Geterotsikl. Soedin., 1985, 1624.
    • (1985) Khim. Geterotsikl. Soedin. , pp. 1624
    • Bubel, O.N.1    Tishchenko, I.G.2    Grinkevich, O.A.3
  • 23
    • 0001076746 scopus 로고
    • Maruokaet al. have reported that exceptionally bulky, oxygenophilic organoaluminum reagent, MABR, is among the most effective reagent for the regio- and stereoselective rearrangement of epoxides into carbonyl compounds: K. Maruoka, T. Ooi and H. Yamamoto, J. Am. Chem. Soc., 1989, 111, 6431; K. Maruoka, J. Sato and H. Yamamoto, J. Am. Chem. Soc., 1991, 113, 5449.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6431
    • Maruoka, K.1    Ooi, T.2    Yamamoto, H.3
  • 24
    • 0000079239 scopus 로고
    • Maruokaet al. have reported that exceptionally bulky, oxygenophilic organoaluminum reagent, MABR, is among the most effective reagent for the regio- and stereoselective rearrangement of epoxides into carbonyl compounds: K. Maruoka, T. Ooi and H. Yamamoto, J. Am. Chem. Soc., 1989, 111, 6431; K. Maruoka, J. Sato and H. Yamamoto, J. Am. Chem. Soc., 1991, 113, 5449.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5449
    • Maruoka, K.1    Sato, J.2    Yamamoto, H.3
  • 32
    • 0034698317 scopus 로고    scopus 로고
    • Many good methods have been available for the preparation of α,β-epoxy ketones. For recent reviews, see: M. J. Porter and J. Skidmore, Chem. Commun., 2000, 1215; T. Nemoto, T. Ohshima and M. Shibasaki, J. Synth. Org. Chem. Jpn., 2000, 60, 94.
    • (2000) Chem. Commun. , pp. 1215
    • Porter, M.J.1    Skidmore, J.2
  • 33
    • 0012943882 scopus 로고    scopus 로고
    • Many good methods have been available for the preparation of α,β-epoxy ketones. For recent reviews, see: M. J. Porter and J. Skidmore, Chem. Commun., 2000, 1215; T. Nemoto, T. Ohshima and M. Shibasaki, J. Synth. Org. Chem. Jpn., 2000, 60, 94.
    • (2000) J. Synth. Org. Chem. Jpn. , vol.60 , pp. 94
    • Nemoto, T.1    Ohshima, T.2    Shibasaki, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.