Activation of selenoglycosides by photoinduced electron transfer

Chemical Communications

Volumn , Issue 2, 1996, Pages 157-158

  Furuta, Toshiaki ^a   Takeuchi, Kazuomi ^a   Iwamura, Michiko ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011217897     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960000157     Document Type: Article

References (18)

1. See the following reviews: (a) C. Pac and H. Sakurai, J. Synth. Org. Chem., Jpn., 1983, 41, 667; (b) S. L. Mattes and S. Farid, in Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York, 1983, vol. 6, p. 233; (c) P. S. Mariano and J. L. Stavinoha, in Synthetic Organic Photochemistry, ed. W. M. Horspool, Plenum, New York, 1984, pp. 145-257; (d) G. J. Kavarnos and N. J. Turro, Chem. Rev., 1986, 86, 401; (e) J. Mattay, Angew. Chem., Int. Ed. Engl., 1987, 26, 825; Synthesis, 1989, 233; (f) J. K. Kochi, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 7, pp. 849-889; (g) A. Albini, M. Mella and M. Freccero, Tetrahedron, 1994, 50, 575.
2. See the following reviews: (a) C. Pac and H. Sakurai, J. Synth. Org. Chem., Jpn., 1983, 41, 667; (b) S. L. Mattes and S. Farid, in Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York, 1983, vol. 6, p. 233; (c) P. S. Mariano and J. L. Stavinoha, in Synthetic Organic Photochemistry, ed. W. M. Horspool, Plenum, New York, 1984, pp. 145-257; (d) G. J. Kavarnos and N. J. Turro, Chem. Rev., 1986, 86, 401; (e) J. Mattay, Angew. Chem., Int. Ed. Engl., 1987, 26, 825; Synthesis, 1989, 233; (f) J. K. Kochi, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 7, pp. 849-889; (g) A. Albini, M. Mella and M. Freccero, Tetrahedron, 1994, 50, 575.
3. See the following reviews: (a) C. Pac and H. Sakurai, J. Synth. Org. Chem., Jpn., 1983, 41, 667; (b) S. L. Mattes and S. Farid, in Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York, 1983, vol. 6, p. 233; (c) P. S. Mariano and J. L. Stavinoha, in Synthetic Organic Photochemistry, ed. W. M. Horspool, Plenum, New York, 1984, pp. 145-257; (d) G. J. Kavarnos and N. J. Turro, Chem. Rev., 1986, 86, 401; (e) J. Mattay, Angew. Chem., Int. Ed. Engl., 1987, 26, 825; Synthesis, 1989, 233; (f) J. K. Kochi, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 7, pp. 849-889; (g) A. Albini, M. Mella and M. Freccero, Tetrahedron, 1994, 50, 575.
4. See the following reviews: (a) C. Pac and H. Sakurai, J. Synth. Org. Chem., Jpn., 1983, 41, 667; (b) S. L. Mattes and S. Farid, in Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York, 1983, vol. 6, p. 233; (c) P. S. Mariano and J. L. Stavinoha, in Synthetic Organic Photochemistry, ed. W. M. Horspool, Plenum, New York, 1984, pp. 145-257; (d) G. J. Kavarnos and N. J. Turro, Chem. Rev., 1986, 86, 401; (e) J. Mattay, Angew. Chem., Int. Ed. Engl., 1987, 26, 825; Synthesis, 1989, 233; (f) J. K. Kochi, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 7, pp. 849-889; (g) A. Albini, M. Mella and M. Freccero, Tetrahedron, 1994, 50, 575.
5. See the following reviews: (a) C. Pac and H. Sakurai, J. Synth. Org. Chem., Jpn., 1983, 41, 667; (b) S. L. Mattes and S. Farid, in Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York, 1983, vol. 6, p. 233; (c) P. S. Mariano and J. L. Stavinoha, in Synthetic Organic Photochemistry, ed. W. M. Horspool, Plenum, New York, 1984, pp. 145-257; (d) G. J. Kavarnos and N. J. Turro, Chem. Rev., 1986, 86, 401; (e) J. Mattay, Angew. Chem., Int. Ed. Engl., 1987, 26, 825; Synthesis, 1989, 233; (f) J. K. Kochi, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 7, pp. 849-889; (g) A. Albini, M. Mella and M. Freccero, Tetrahedron, 1994, 50, 575.
6. See the following reviews: (a) C. Pac and H. Sakurai, J. Synth. Org. Chem., Jpn., 1983, 41, 667; (b) S. L. Mattes and S. Farid, in Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York, 1983, vol. 6, p. 233; (c) P. S. Mariano and J. L. Stavinoha, in Synthetic Organic Photochemistry, ed. W. M. Horspool, Plenum, New York, 1984, pp. 145-257; (d) G. J. Kavarnos and N. J. Turro, Chem. Rev., 1986, 86, 401; (e) J. Mattay, Angew. Chem., Int. Ed. Engl., 1987, 26, 825; Synthesis, 1989, 233; (f) J. K. Kochi, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 7, pp. 849-889; (g) A. Albini, M. Mella and M. Freccero, Tetrahedron, 1994, 50, 575.
7. See the following reviews: (a) C. Pac and H. Sakurai, J. Synth. Org. Chem., Jpn., 1983, 41, 667; (b) S. L. Mattes and S. Farid, in Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York, 1983, vol. 6, p. 233; (c) P. S. Mariano and J. L. Stavinoha, in Synthetic Organic Photochemistry, ed. W. M. Horspool, Plenum, New York, 1984, pp. 145-257; (d) G. J. Kavarnos and N. J. Turro, Chem. Rev., 1986, 86, 401; (e) J. Mattay, Angew. Chem., Int. Ed. Engl., 1987, 26, 825; Synthesis, 1989, 233; (f) J. K. Kochi, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 7, pp. 849-889; (g) A. Albini, M. Mella and M. Freccero, Tetrahedron, 1994, 50, 575.
8. See the following reviews: (a) C. Pac and H. Sakurai, J. Synth. Org. Chem., Jpn., 1983, 41, 667; (b) S. L. Mattes and S. Farid, in Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York, 1983, vol. 6, p. 233; (c) P. S. Mariano and J. L. Stavinoha, in Synthetic Organic Photochemistry, ed. W. M. Horspool, Plenum, New York, 1984, pp. 145-257; (d) G. J. Kavarnos and N. J. Turro, Chem. Rev., 1986, 86, 401; (e) J. Mattay, Angew. Chem., Int. Ed. Engl., 1987, 26, 825; Synthesis, 1989, 233; (f) J. K. Kochi, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 7, pp. 849-889; (g) A. Albini, M. Mella and M. Freccero, Tetrahedron, 1994, 50, 575.
9. Selected reviews: R. R. Schmidt, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 6, pp. 33-64; K. Toshima and K. Tatsuta, Chem. Rev., 1993, 93, 1503 and references cited therein.
10. Selected reviews: R. R. Schmidt, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 6, pp. 33-64; K. Toshima and K. Tatsuta, Chem. Rev., 1993, 93, 1503 and references cited therein.
11. Selected references for ground state SET glycosylation induced by anodic oxidation: R. Noyori and I. Kurimoto, J. Org. Chem., 1986, 51, 4322; C. Amatore, A. Jutand, J.-M. Mallet, G. Meyer and P. Sinay, J. Chem Soc., Chem. Commun., 1990, 718; G. Balavoine, A. Gref, J.-C. Fischer and A. Lubineau, Tetrahedron Lett., 1990, 31, 5761; by one electron oxidizing reagent: A. Marra, J.-M. Mallet, C. Amatore and P. Sinay, Synlett. 1990, 572.
12. Selected references for ground state SET glycosylation induced by anodic oxidation: R. Noyori and I. Kurimoto, J. Org. Chem., 1986, 51, 4322; C. Amatore, A. Jutand, J.-M. Mallet, G. Meyer and P. Sinay, J. Chem Soc., Chem. Commun., 1990, 718; G. Balavoine, A. Gref, J.-C. Fischer and A. Lubineau, Tetrahedron Lett., 1990, 31, 5761; by one electron oxidizing reagent: A. Marra, J.-M. Mallet, C. Amatore and P. Sinay, Synlett. 1990, 572.
13. Selected references for ground state SET glycosylation induced by anodic oxidation: R. Noyori and I. Kurimoto, J. Org. Chem., 1986, 51, 4322; C. Amatore, A. Jutand, J.-M. Mallet, G. Meyer and P. Sinay, J. Chem Soc., Chem. Commun., 1990, 718; G. Balavoine, A. Gref, J.-C. Fischer and A. Lubineau, Tetrahedron Lett., 1990, 31, 5761; by one electron oxidizing reagent: A. Marra, J.-M. Mallet, C. Amatore and P. Sinay, Synlett. 1990, 572.
14. Selected references for ground state SET glycosylation induced by anodic oxidation: R. Noyori and I. Kurimoto, J. Org. Chem., 1986, 51, 4322; C. Amatore, A. Jutand, J.-M. Mallet, G. Meyer and P. Sinay, J. Chem Soc., Chem. Commun., 1990, 718; G. Balavoine, A. Gref, J.-C. Fischer and A. Lubineau, Tetrahedron Lett., 1990, 31, 5761; by one electron oxidizing reagent: A. Marra, J.-M. Mallet, C. Amatore and P. Sinay, Synlett. 1990, 572.
15. S. Hashimoto, I. Kurimoto, Y. Fujii and R. Noyori, J. Am. Chem. Soc., 1985, 107, 1427.
16. G. Pandey, B. B. V. Soma Sekhar and U. T. Bhalerao, J. Am. Chem. Soc., 1990, 112, 5650; G. Pandey and B. B. V. Soma Sekhar, J. Org. Chem., 1994, 59, 7367.
17. G. Pandey, B. B. V. Soma Sekhar and U. T. Bhalerao, J. Am. Chem. Soc., 1990, 112, 5650; G. Pandey and B. B. V. Soma Sekhar, J. Org. Chem., 1994, 59, 7367.
18. D. Rehm and A. Weller, Isr. J. Chem., 1970, 8, 259.