메뉴 건너뛰기




Volumn 54, Issue 3, 1996, Pages 166-175

Recent Advances in Synthetic Reactions Using Organoselenium Reagents

Author keywords

Asymmetric oxyselenenylation; Catalytic oxyselenenylation deselenenylation; Electrophilic selenium reagent; Methoxyselenenylation; Selenium; Selenoetherification; Selenolactonization

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHEMICAL BONDS; MOLECULAR STRUCTURE; OLEFINS; OXIDATION; SYNTHESIS (CHEMICAL);

EID: 0030107946     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.54.166     Document Type: Article
Times cited : (11)

References (69)
  • 3
    • 0001537818 scopus 로고
    • K.B. Sharpless, R.P. Lauer, J. Org. Chem., 39, 429 (1974) ; P.G. Gassman, A. Miura, T. Miura, ibid., 47, 951 (1982) ; S. Tomoda, Y. Takeuchi, Y. Nomura, Tetrahedron Lett., 23, 1361 (1982) ; idem J. Chem. Soc., Chem. Commun., 1980, 871 ; idem, Chem. Lett., 1982, 1733 ; T. Hayama, S. Tomoda, Y. Takeuchi, Y. Nomura, Tetrahedron Lett., 23, 4733 (1982)
    • (1974) J. Org. Chem. , vol.39 , pp. 429
    • Sharpless, K.B.1    Lauer, R.P.2
  • 4
    • 0001189811 scopus 로고
    • K.B. Sharpless, R.P. Lauer, J. Org. Chem., 39, 429 (1974) ; P.G. Gassman, A. Miura, T. Miura, ibid., 47, 951 (1982) ; S. Tomoda, Y. Takeuchi, Y. Nomura, Tetrahedron Lett., 23, 1361 (1982) ; idem J. Chem. Soc., Chem. Commun., 1980, 871 ; idem, Chem. Lett., 1982, 1733 ; T. Hayama, S. Tomoda, Y. Takeuchi, Y. Nomura, Tetrahedron Lett., 23, 4733 (1982)
    • (1982) J. Org. Chem. , vol.47 , pp. 951
    • Gassman, P.G.1    Miura, A.2    Miura, T.3
  • 5
    • 0000948589 scopus 로고
    • K.B. Sharpless, R.P. Lauer, J. Org. Chem., 39, 429 (1974) ; P.G. Gassman, A. Miura, T. Miura, ibid., 47, 951 (1982) ; S. Tomoda, Y. Takeuchi, Y. Nomura, Tetrahedron Lett., 23, 1361 (1982) ; idem J. Chem. Soc., Chem. Commun., 1980, 871 ; idem, Chem. Lett., 1982, 1733 ; T. Hayama, S. Tomoda, Y. Takeuchi, Y. Nomura, Tetrahedron Lett., 23, 4733 (1982)
    • (1982) Tetrahedron Lett. , vol.23 , pp. 1361
    • Tomoda, S.1    Takeuchi, Y.2    Nomura, Y.3
  • 6
    • 0001537818 scopus 로고
    • K.B. Sharpless, R.P. Lauer, J. Org. Chem., 39, 429 (1974) ; P.G. Gassman, A. Miura, T. Miura, ibid., 47, 951 (1982) ; S. Tomoda, Y. Takeuchi, Y. Nomura, Tetrahedron Lett., 23, 1361 (1982) ; idem J. Chem. Soc., Chem. Commun., 1980, 871 ; idem, Chem. Lett., 1982, 1733 ; T. Hayama, S. Tomoda, Y. Takeuchi, Y. Nomura, Tetrahedron Lett., 23, 4733 (1982)
    • (1980) J. Chem. Soc., Chem. Commun. , pp. 871
    • Tomoda, S.1    Takeuchi, Y.2    Nomura, Y.3
  • 7
    • 0001537818 scopus 로고
    • K.B. Sharpless, R.P. Lauer, J. Org. Chem., 39, 429 (1974) ; P.G. Gassman, A. Miura, T. Miura, ibid., 47, 951 (1982) ; S. Tomoda, Y. Takeuchi, Y. Nomura, Tetrahedron Lett., 23, 1361 (1982) ; idem J. Chem. Soc., Chem. Commun., 1980, 871 ; idem, Chem. Lett., 1982, 1733 ; T. Hayama, S. Tomoda, Y. Takeuchi, Y. Nomura, Tetrahedron Lett., 23, 4733 (1982)
    • (1982) Chem. Lett. , pp. 1733
    • Tomoda, S.1    Takeuchi, Y.2    Nomura, Y.3
  • 8
    • 0001446498 scopus 로고
    • K.B. Sharpless, R.P. Lauer, J. Org. Chem., 39, 429 (1974) ; P.G. Gassman, A. Miura, T. Miura, ibid., 47, 951 (1982) ; S. Tomoda, Y. Takeuchi, Y. Nomura, Tetrahedron Lett., 23, 1361 (1982) ; idem J. Chem. Soc., Chem. Commun., 1980, 871 ; idem, Chem. Lett., 1982, 1733 ; T. Hayama, S. Tomoda, Y. Takeuchi, Y. Nomura, Tetrahedron Lett., 23, 4733 (1982)
    • (1982) Tetrahedron Lett. , vol.23 , pp. 4733
    • Hayama, T.1    Tomoda, S.2    Takeuchi, Y.3    Nomura, Y.4
  • 9
    • 2742512883 scopus 로고
    • K.B. Sharpless, R. F. Lauer, J. Am. Chem. Soc., 36, 2561 (1971) ; K. B. Sharpless, M. W. Young, R. F. Lauer, Tetrahedron Lett., 1973, 1979 ; T. Hori, K.B. Sharpless, J. Org. Chem., 43, 1689 (1978)
    • (1971) J. Am. Chem. Soc. , vol.36 , pp. 2561
    • Sharpless, K.B.1    Lauer, R.F.2
  • 10
    • 0001697534 scopus 로고
    • K.B. Sharpless, R. F. Lauer, J. Am. Chem. Soc., 36, 2561 (1971) ; K. B. Sharpless, M. W. Young, R. F. Lauer, Tetrahedron Lett., 1973, 1979 ; T. Hori, K.B. Sharpless, J. Org. Chem., 43, 1689 (1978)
    • (1973) Tetrahedron Lett. , pp. 1979
    • Sharpless, K.B.1    Young, M.W.2    Lauer, R.F.3
  • 11
    • 33947092633 scopus 로고
    • K.B. Sharpless, R. F. Lauer, J. Am. Chem. Soc., 36, 2561 (1971) ; K. B. Sharpless, M. W. Young, R. F. Lauer, Tetrahedron Lett., 1973, 1979 ; T. Hori, K.B. Sharpless, J. Org. Chem., 43, 1689 (1978)
    • (1978) J. Org. Chem. , vol.43 , pp. 1689
    • Hori, T.1    Sharpless, K.B.2
  • 12
    • 33847086153 scopus 로고
    • M.F. Semmelhack, S. Tomoda, H. Nagaoka, S. Boettger, K.M. Hurst, J. Am. Chem. Soc., 102, 7567 (1980), G. Majetich, J.-S. Song, A. J. Leigh, S.M. Condon, J. Org. Chem., 58, 1030 (1993) ; G. Blay, L. Cardona, B. Garcia, J.R. Pedro, ibid., 58, 7204 (1993) ; K. M. Mattia, B. Ganen, ibid., 59, 720 (1994) ; K. R. Dahnke, L. A. Paquette, ibid., 59, 885 (1994)
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 7567
    • Semmelhack, M.F.1    Tomoda, S.2    Nagaoka, H.3    Boettger, S.4    Hurst, K.M.5
  • 13
    • 0001436624 scopus 로고
    • M.F. Semmelhack, S. Tomoda, H. Nagaoka, S. Boettger, K.M. Hurst, J. Am. Chem. Soc., 102, 7567 (1980), G. Majetich, J.-S. Song, A. J. Leigh, S.M. Condon, J. Org. Chem., 58, 1030 (1993) ; G. Blay, L. Cardona, B. Garcia, J.R. Pedro, ibid., 58, 7204 (1993) ; K. M. Mattia, B. Ganen, ibid., 59, 720 (1994) ; K. R. Dahnke, L. A. Paquette, ibid., 59, 885 (1994)
    • (1993) J. Org. Chem. , vol.58 , pp. 1030
    • Majetich, G.1    Song, J.-S.2    Leigh, A.J.3    Condon, S.M.4
  • 14
    • 0000540970 scopus 로고
    • M.F. Semmelhack, S. Tomoda, H. Nagaoka, S. Boettger, K.M. Hurst, J. Am. Chem. Soc., 102, 7567 (1980), G. Majetich, J.-S. Song, A. J. Leigh, S.M. Condon, J. Org. Chem., 58, 1030 (1993) ; G. Blay, L. Cardona, B. Garcia, J.R. Pedro, ibid., 58, 7204 (1993) ; K. M. Mattia, B. Ganen, ibid., 59, 720 (1994) ; K. R. Dahnke, L. A. Paquette, ibid., 59, 885 (1994)
    • (1993) J. Org. Chem. , vol.58 , pp. 7204
    • Blay, G.1    Cardona, L.2    Garcia, B.3    Pedro, J.R.4
  • 15
    • 0028267069 scopus 로고
    • M.F. Semmelhack, S. Tomoda, H. Nagaoka, S. Boettger, K.M. Hurst, J. Am. Chem. Soc., 102, 7567 (1980), G. Majetich, J.-S. Song, A. J. Leigh, S.M. Condon, J. Org. Chem., 58, 1030 (1993) ; G. Blay, L. Cardona, B. Garcia, J.R. Pedro, ibid., 58, 7204 (1993) ; K. M. Mattia, B. Ganen, ibid., 59, 720 (1994) ; K. R. Dahnke, L. A. Paquette, ibid., 59, 885 (1994)
    • (1994) J. Org. Chem. , vol.59 , pp. 720
    • Mattia, K.M.1    Ganen, B.2
  • 16
    • 0028353349 scopus 로고
    • M.F. Semmelhack, S. Tomoda, H. Nagaoka, S. Boettger, K.M. Hurst, J. Am. Chem. Soc., 102, 7567 (1980), G. Majetich, J.-S. Song, A. J. Leigh, S.M. Condon, J. Org. Chem., 58, 1030 (1993) ; G. Blay, L. Cardona, B. Garcia, J.R. Pedro, ibid., 58, 7204 (1993) ; K. M. Mattia, B. Ganen, ibid., 59, 720 (1994) ; K. R. Dahnke, L. A. Paquette, ibid., 59, 885 (1994)
    • (1994) J. Org. Chem. , vol.59 , pp. 885
    • Dahnke, K.R.1    Paquette, L.A.2
  • 17
    • 37049102411 scopus 로고
    • D. J. Clive, G. Chittattu, N. J. Curtis, W. A. Kiel, C. K. Wong, J. Chem. Soc., Chem. Commun., 1977, 725 ; D. Goldsmith, D. Liotta, C. Lee, G. Zima, Tetrahedron Lett., 50, 4801 (1979) ; K.C. Nicolaou, S. P. Seitz, W. J. Sipio, J. F. Blount, J. Am. Chem. Sac., 101, 3884 (1979) ; K. C. Nicolaou, R. L. Magolda, W.J. Sipio, W.E. Barnette, Z. Lysenko, M.M. Joullie, ibid., 102, 3784 (1980)
    • (1977) J. Chem. Soc., Chem. Commun. , pp. 725
    • Clive, D.J.1    Chittattu, G.2    Curtis, N.J.3    Kiel, W.A.4    Wong, C.K.5
  • 18
    • 0001406164 scopus 로고
    • D. J. Clive, G. Chittattu, N. J. Curtis, W. A. Kiel, C. K. Wong, J. Chem. Soc., Chem. Commun., 1977, 725 ; D. Goldsmith, D. Liotta, C. Lee, G. Zima, Tetrahedron Lett., 50, 4801 (1979) ; K.C. Nicolaou, S. P. Seitz, W. J. Sipio, J. F. Blount, J. Am. Chem. Sac., 101, 3884 (1979) ; K. C. Nicolaou, R. L. Magolda, W.J. Sipio, W.E. Barnette, Z. Lysenko, M.M. Joullie, ibid., 102, 3784 (1980)
    • (1979) Tetrahedron Lett. , vol.50 , pp. 4801
    • Goldsmith, D.1    Liotta, D.2    Lee, C.3    Zima, G.4
  • 19
    • 33845560828 scopus 로고
    • D. J. Clive, G. Chittattu, N. J. Curtis, W. A. Kiel, C. K. Wong, J. Chem. Soc., Chem. Commun., 1977, 725 ; D. Goldsmith, D. Liotta, C. Lee, G. Zima, Tetrahedron Lett., 50, 4801 (1979) ; K.C. Nicolaou, S. P. Seitz, W. J. Sipio, J. F. Blount, J. Am. Chem. Sac., 101, 3884 (1979) ; K. C. Nicolaou, R. L. Magolda, W.J. Sipio, W.E. Barnette, Z. Lysenko, M.M. Joullie, ibid., 102, 3784 (1980)
    • (1979) J. Am. Chem. Sac. , vol.101 , pp. 3884
    • Nicolaou, K.C.1    Seitz, S.P.2    Sipio, W.J.3    Blount, J.F.4
  • 20
    • 0001588031 scopus 로고
    • D. J. Clive, G. Chittattu, N. J. Curtis, W. A. Kiel, C. K. Wong, J. Chem. Soc., Chem. Commun., 1977, 725 ; D. Goldsmith, D. Liotta, C. Lee, G. Zima, Tetrahedron Lett., 50, 4801 (1979) ; K.C. Nicolaou, S. P. Seitz, W. J. Sipio, J. F. Blount, J. Am. Chem. Sac., 101, 3884 (1979) ; K. C. Nicolaou, R. L. Magolda, W.J. Sipio, W.E. Barnette, Z. Lysenko, M.M. Joullie, ibid., 102, 3784 (1980)
    • (1980) J. Am. Chem. Sac. , vol.102 , pp. 3784
    • Nicolaou, K.C.1    Magolda, R.L.2    Sipio, W.J.3    Barnette, W.E.4    Lysenko, Z.5    Joullie, M.M.6
  • 22
    • 49349139760 scopus 로고
    • D.L.J. Clive, Tetrahedron, 34, 1049 (1978) ; H.J. Reich, Acc. Chem. Res., 12, 22 (1979) ; K.C. Nicolaou, Tetrahedron, 37, 4097 (1981) ; N. Sonoda, A. Ogawa, "Functional Groups Containing Selenium and Tellurium in Various Oxidation States" in The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 1, ed. by S. Patai, Z. Rappoport, John Wiley & Sons (1986) ; D. Liotta, Acc. Chem. Res., 17, 28 (1984) ; S. Tomoda, Y. Usuki, K. Fujuta, M. Iwaoka, Rev. Heteroatom Chem., 4, 249 (1991)
    • (1978) Tetrahedron , vol.34 , pp. 1049
    • Clive, D.L.J.1
  • 23
    • 0002389988 scopus 로고
    • D.L.J. Clive, Tetrahedron, 34, 1049 (1978) ; H.J. Reich, Acc. Chem. Res., 12, 22 (1979) ; K.C. Nicolaou, Tetrahedron, 37, 4097 (1981) ; N. Sonoda, A. Ogawa, "Functional Groups Containing Selenium and Tellurium in Various Oxidation States" in The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 1, ed. by S. Patai, Z. Rappoport, John Wiley & Sons (1986) ; D. Liotta, Acc. Chem. Res., 17, 28 (1984) ; S. Tomoda, Y. Usuki, K. Fujuta, M. Iwaoka, Rev. Heteroatom Chem., 4, 249 (1991)
    • (1979) Acc. Chem. Res. , vol.12 , pp. 22
    • Reich, H.J.1
  • 24
    • 0000388648 scopus 로고
    • D.L.J. Clive, Tetrahedron, 34, 1049 (1978) ; H.J. Reich, Acc. Chem. Res., 12, 22 (1979) ; K.C. Nicolaou, Tetrahedron, 37, 4097 (1981) ; N. Sonoda, A. Ogawa, "Functional Groups Containing Selenium and Tellurium in Various Oxidation States" in The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 1, ed. by S. Patai, Z. Rappoport, John Wiley & Sons (1986) ; D. Liotta, Acc. Chem. Res., 17, 28 (1984) ; S. Tomoda, Y. Usuki, K. Fujuta, M. Iwaoka, Rev. Heteroatom Chem., 4, 249 (1991)
    • (1981) Tetrahedron , vol.37 , pp. 4097
    • Nicolaou, K.C.1
  • 25
    • 49349139760 scopus 로고
    • Functional Groups Containing Selenium and Tellurium in Various Oxidation States
    • ed. by S. Patai, Z. Rappoport, John Wiley & Sons
    • D.L.J. Clive, Tetrahedron, 34, 1049 (1978) ; H.J. Reich, Acc. Chem. Res., 12, 22 (1979) ; K.C. Nicolaou, Tetrahedron, 37, 4097 (1981) ; N. Sonoda, A. Ogawa, "Functional Groups Containing Selenium and Tellurium in Various Oxidation States" in The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 1, ed. by S. Patai, Z. Rappoport, John Wiley & Sons (1986) ; D. Liotta, Acc. Chem. Res., 17, 28 (1984) ; S. Tomoda, Y. Usuki, K. Fujuta, M. Iwaoka, Rev. Heteroatom Chem., 4, 249 (1991)
    • (1986) The Chemistry of Organic Selenium and Tellurium Compounds , vol.1
    • Sonoda, N.1    Ogawa, A.2
  • 26
    • 0002756772 scopus 로고
    • D.L.J. Clive, Tetrahedron, 34, 1049 (1978) ; H.J. Reich, Acc. Chem. Res., 12, 22 (1979) ; K.C. Nicolaou, Tetrahedron, 37, 4097 (1981) ; N. Sonoda, A. Ogawa, "Functional Groups Containing Selenium and Tellurium in Various Oxidation States" in The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 1, ed. by S. Patai, Z. Rappoport, John Wiley & Sons (1986) ; D. Liotta, Acc. Chem. Res., 17, 28 (1984) ; S. Tomoda, Y. Usuki, K. Fujuta, M. Iwaoka, Rev. Heteroatom Chem., 4, 249 (1991)
    • (1984) Acc. Chem. Res. , vol.17 , pp. 28
    • Liotta, D.1
  • 27
    • 49349139760 scopus 로고
    • D.L.J. Clive, Tetrahedron, 34, 1049 (1978) ; H.J. Reich, Acc. Chem. Res., 12, 22 (1979) ; K.C. Nicolaou, Tetrahedron, 37, 4097 (1981) ; N. Sonoda, A. Ogawa, "Functional Groups Containing Selenium and Tellurium in Various Oxidation States" in The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 1, ed. by S. Patai, Z. Rappoport, John Wiley & Sons (1986) ; D. Liotta, Acc. Chem. Res., 17, 28 (1984) ; S. Tomoda, Y. Usuki, K. Fujuta, M. Iwaoka, Rev. Heteroatom Chem., 4, 249 (1991)
    • (1991) Rev. Heteroatom Chem. , vol.4 , pp. 249
    • Tomoda, S.1    Usuki, Y.2    Fujuta, K.3    Iwaoka, M.4
  • 28
    • 0343652996 scopus 로고
    • ed. by W. Tarahanovsky, Academic Press, N.Y.
    • H.J. Reich, "Oxidation in Organic Chemistry : Pt. C,"ed. by W. Tarahanovsky, Academic Press, N.Y. (1978), p. 1 ; K.C. Nicolaou, N.A. Petasis, "Selenium in Natural Products Synthesis", CIS Inc., Philadelphia PA (1984) ; C. Paulmier, "Selenium Reagents and Intermediates in Organic Synthesis", Pergamon Press, Oxford, N. Y. (1986)
    • (1978) Oxidation in Organic Chemistry : Pt. c , pp. 1
    • Reich, H.J.1
  • 29
    • 0004189194 scopus 로고
    • CIS Inc., Philadelphia PA
    • H.J. Reich, "Oxidation in Organic Chemistry : Pt. C,"ed. by W. Tarahanovsky, Academic Press, N.Y. (1978), p. 1 ; K.C. Nicolaou, N.A. Petasis, "Selenium in Natural Products Synthesis", CIS Inc., Philadelphia PA (1984) ; C. Paulmier, "Selenium Reagents and Intermediates in Organic Synthesis", Pergamon Press, Oxford, N. Y. (1986)
    • (1984) Selenium in Natural Products Synthesis
    • Nicolaou, K.C.1    Petasis, N.A.2
  • 30
    • 2742593059 scopus 로고
    • Pergamon Press, Oxford, N. Y.
    • H.J. Reich, "Oxidation in Organic Chemistry : Pt. C,"ed. by W. Tarahanovsky, Academic Press, N.Y. (1978), p. 1 ; K.C. Nicolaou, N.A. Petasis, "Selenium in Natural Products Synthesis", CIS Inc., Philadelphia PA (1984) ; C. Paulmier, "Selenium Reagents and Intermediates in Organic Synthesis", Pergamon Press, Oxford, N. Y. (1986)
    • (1986) Selenium Reagents and
    • Paulmier, C.1    Synthesis, I.I.O.2
  • 36
    • 85033770872 scopus 로고    scopus 로고
    • Japanese source


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.