Use of O,Se-acetals for radical-mediated phenylseleno group transfer reactions

Synthesis

Volumn , Issue 2, 1996, Pages 253-258

  Renaud, Philippe ^a   Abazi, Sokol ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

phenylseleno transfer; radicals; selenium; hydroxy acids

Indexed keywords

ORGANOSELENIUM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029874181     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4182     Document Type: Article

References (27)

1. Paulmier, G. Selenium Reagents and Intermediates in Organic Chemistry; Pergamon: Oxford, 1986. Liotta, D. Organoselenium Chemistry, Wiley: New York, 1987. Clive, D.L. J. Tetrahedron 1978, 34, 1049.
2. Paulmier, G. Selenium Reagents and Intermediates in Organic Chemistry; Pergamon: Oxford, 1986. Liotta, D. Organoselenium Chemistry, Wiley: New York, 1987. Clive, D.L. J. Tetrahedron 1978, 34, 1049.
3. Paulmier, G. Selenium Reagents and Intermediates in Organic Chemistry; Pergamon: Oxford, 1986. Liotta, D. Organoselenium Chemistry, Wiley: New York, 1987. Clive, D.L. J. Tetrahedron 1978, 34, 1049.
4. De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157.
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6. Byers, J.H.; Lane, G.C. Tetrahedron Lett. 1990, 31, 5697. Byers, J.H.; Gleason, T.G.; Knight, K.S. J. Chem. Soc., Chem. Commun. 1991, 354. Byers, J.H.; Harper, B.C. Tetrahedron Lett. 1992, 33, 6953. Byers, J.H.; Lane, G.C. J. Org. Chem. 1993, 58, 3355. For other applications of phenylseleno group transfer reaction for the formation of C - C bonds see: Curran, D.P.; Thoma, G. J. Am. Chem. Soc. 1992, 14, 4436. Curran, D.P.; Shu, M. Bull. Soc. Chim. Fr. 1993, 130, 314. Curran, D.P.; Geib, S.J.; Kuo, L.H. Tetrahedron Lett. 1994, 35, 6235. Curran, D.P.; Eichenberger, E.; Collis, M.; Roepel, M.G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279.
7. Byers, J.H.; Lane, G.C. Tetrahedron Lett. 1990, 31, 5697. Byers, J.H.; Gleason, T.G.; Knight, K.S. J. Chem. Soc., Chem. Commun. 1991, 354. Byers, J.H.; Harper, B.C. Tetrahedron Lett. 1992, 33, 6953. Byers, J.H.; Lane, G.C. J. Org. Chem. 1993, 58, 3355. For other applications of phenylseleno group transfer reaction for the formation of C - C bonds see: Curran, D.P.; Thoma, G. J. Am. Chem. Soc. 1992, 14, 4436. Curran, D.P.; Shu, M. Bull. Soc. Chim. Fr. 1993, 130, 314. Curran, D.P.; Geib, S.J.; Kuo, L.H. Tetrahedron Lett. 1994, 35, 6235. Curran, D.P.; Eichenberger, E.; Collis, M.; Roepel, M.G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279.
8. Byers, J.H.; Lane, G.C. Tetrahedron Lett. 1990, 31, 5697. Byers, J.H.; Gleason, T.G.; Knight, K.S. J. Chem. Soc., Chem. Commun. 1991, 354. Byers, J.H.; Harper, B.C. Tetrahedron Lett. 1992, 33, 6953. Byers, J.H.; Lane, G.C. J. Org. Chem. 1993, 58, 3355. For other applications of phenylseleno group transfer reaction for the formation of C - C bonds see: Curran, D.P.; Thoma, G. J. Am. Chem. Soc. 1992, 14, 4436. Curran, D.P.; Shu, M. Bull. Soc. Chim. Fr. 1993, 130, 314. Curran, D.P.; Geib, S.J.; Kuo, L.H. Tetrahedron Lett. 1994, 35, 6235. Curran, D.P.; Eichenberger, E.; Collis, M.; Roepel, M.G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279.
9. Byers, J.H.; Lane, G.C. Tetrahedron Lett. 1990, 31, 5697. Byers, J.H.; Gleason, T.G.; Knight, K.S. J. Chem. Soc., Chem. Commun. 1991, 354. Byers, J.H.; Harper, B.C. Tetrahedron Lett. 1992, 33, 6953. Byers, J.H.; Lane, G.C. J. Org. Chem. 1993, 58, 3355. For other applications of phenylseleno group transfer reaction for the formation of C - C bonds see: Curran, D.P.; Thoma, G. J. Am. Chem. Soc. 1992, 14, 4436. Curran, D.P.; Shu, M. Bull. Soc. Chim. Fr. 1993, 130, 314. Curran, D.P.; Geib, S.J.; Kuo, L.H. Tetrahedron Lett. 1994, 35, 6235. Curran, D.P.; Eichenberger, E.; Collis, M.; Roepel, M.G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279.
10. Byers, J.H.; Lane, G.C. Tetrahedron Lett. 1990, 31, 5697. Byers, J.H.; Gleason, T.G.; Knight, K.S. J. Chem. Soc., Chem. Commun. 1991, 354. Byers, J.H.; Harper, B.C. Tetrahedron Lett. 1992, 33, 6953. Byers, J.H.; Lane, G.C. J. Org. Chem. 1993, 58, 3355. For other applications of phenylseleno group transfer reaction for the formation of C - C bonds see: Curran, D.P.; Thoma, G. J. Am. Chem. Soc. 1992, 14, 4436. Curran, D.P.; Shu, M. Bull. Soc. Chim. Fr. 1993, 130, 314. Curran, D.P.; Geib, S.J.; Kuo, L.H. Tetrahedron Lett. 1994, 35, 6235. Curran, D.P.; Eichenberger, E.; Collis, M.; Roepel, M.G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279.
11. Byers, J.H.; Lane, G.C. Tetrahedron Lett. 1990, 31, 5697. Byers, J.H.; Gleason, T.G.; Knight, K.S. J. Chem. Soc., Chem. Commun. 1991, 354. Byers, J.H.; Harper, B.C. Tetrahedron Lett. 1992, 33, 6953. Byers, J.H.; Lane, G.C. J. Org. Chem. 1993, 58, 3355. For other applications of phenylseleno group transfer reaction for the formation of C - C bonds see: Curran, D.P.; Thoma, G. J. Am. Chem. Soc. 1992, 14, 4436. Curran, D.P.; Shu, M. Bull. Soc. Chim. Fr. 1993, 130, 314. Curran, D.P.; Geib, S.J.; Kuo, L.H. Tetrahedron Lett. 1994, 35, 6235. Curran, D.P.; Eichenberger, E.; Collis, M.; Roepel, M.G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279.
12. Byers, J.H.; Lane, G.C. Tetrahedron Lett. 1990, 31, 5697. Byers, J.H.; Gleason, T.G.; Knight, K.S. J. Chem. Soc., Chem. Commun. 1991, 354. Byers, J.H.; Harper, B.C. Tetrahedron Lett. 1992, 33, 6953. Byers, J.H.; Lane, G.C. J. Org. Chem. 1993, 58, 3355. For other applications of phenylseleno group transfer reaction for the formation of C - C bonds see: Curran, D.P.; Thoma, G. J. Am. Chem. Soc. 1992, 14, 4436. Curran, D.P.; Shu, M. Bull. Soc. Chim. Fr. 1993, 130, 314. Curran, D.P.; Geib, S.J.; Kuo, L.H. Tetrahedron Lett. 1994, 35, 6235. Curran, D.P.; Eichenberger, E.; Collis, M.; Roepel, M.G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279.
13. Byers, J.H.; Lane, G.C. Tetrahedron Lett. 1990, 31, 5697. Byers, J.H.; Gleason, T.G.; Knight, K.S. J. Chem. Soc., Chem. Commun. 1991, 354. Byers, J.H.; Harper, B.C. Tetrahedron Lett. 1992, 33, 6953. Byers, J.H.; Lane, G.C. J. Org. Chem. 1993, 58, 3355. For other applications of phenylseleno group transfer reaction for the formation of C - C bonds see: Curran, D.P.; Thoma, G. J. Am. Chem. Soc. 1992, 14, 4436. Curran, D.P.; Shu, M. Bull. Soc. Chim. Fr. 1993, 130, 314. Curran, D.P.; Geib, S.J.; Kuo, L.H. Tetrahedron Lett. 1994, 35, 6235. Curran, D.P.; Eichenberger, E.; Collis, M.; Roepel, M.G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279.
14. Renaud, P.; Vionnet, J.-P. J. Org. Chem. 1993, 58, 5895. Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. For a related paper see: Renaud, P.; Vionnet, J.-P. Chimia 1994, 48, 471.
15. Renaud, P.; Vionnet, J.-P. J. Org. Chem. 1993, 58, 5895. Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. For a related paper see: Renaud, P.; Vionnet, J.-P. Chimia 1994, 48, 471.
16. Renaud, P.; Vionnet, J.-P. J. Org. Chem. 1993, 58, 5895. Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. For a related paper see: Renaud, P.; Vionnet, J.-P. Chimia 1994, 48, 471.
17. For related work using chlorine atom transfer: Udding, J.H.; Hiemstra, H.; Van Zanden, M.N.A.; Speckamp, W.N. Tetrahedron Lett. 1991, 32, 3123. Udding, J.H.; Hiemstra, H.; Speckamp, W.N. J. Chem. Soc., Perkin Trans. 2 1992, 1529. Udding, J.H.; Hiemstra, H.; Fraanje, J.; Goubitz, K.; Spekkamp, W.N.; Kaptein, B.; Schoemaker, H.E.; Kamphuis, J. Tetrahedron: Asymmetry 1993, 4, 425.
18. For related work using chlorine atom transfer: Udding, J.H.; Hiemstra, H.; Van Zanden, M.N.A.; Speckamp, W.N. Tetrahedron Lett. 1991, 32, 3123. Udding, J.H.; Hiemstra, H.; Speckamp, W.N. J. Chem. Soc., Perkin Trans. 2 1992, 1529. Udding, J.H.; Hiemstra, H.; Fraanje, J.; Goubitz, K.; Spekkamp, W.N.; Kaptein, B.; Schoemaker, H.E.; Kamphuis, J. Tetrahedron: Asymmetry 1993, 4, 425.
19. For related work using chlorine atom transfer: Udding, J.H.; Hiemstra, H.; Van Zanden, M.N.A.; Speckamp, W.N. Tetrahedron Lett. 1991, 32, 3123. Udding, J.H.; Hiemstra, H.; Speckamp, W.N. J. Chem. Soc., Perkin Trans. 2 1992, 1529. Udding, J.H.; Hiemstra, H.; Fraanje, J.; Goubitz, K.; Spekkamp, W.N.; Kaptein, B.; Schoemaker, H.E.; Kamphuis, J. Tetrahedron: Asymmetry 1993, 4, 425.
20. Transfer of xanthates has also been reported: Udding, J.H.; Giesselink, J.P.M.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1994, 59, 6671. Udding, J.H.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1994, 59, 3721.
21. Transfer of xanthates has also been reported: Udding, J.H.; Giesselink, J.P.M.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1994, 59, 6671. Udding, J.H.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1994, 59, 3721.
22. For a discussion of the reactivity of captodative radicals, see: Viehe, H.G.; Janousek, Z.; Merény, R.; Stella, L. Acc. Chem. Res. 1985, 18, 148.
23. For radical dimerization using α-phenylselanyl esters, see: Porter, N.A.; Qi Su; Harp, J.J.; Rosenstein, I.J.; McPhail, A.T. Tetrahedron Lett. 1993, 34, 4457. Porter, N.A.; Rosenstein, I.J. Tetrahedron Lett. 1993, 34, 7865.
24. For radical dimerization using α-phenylselanyl esters, see: Porter, N.A.; Qi Su; Harp, J.J.; Rosenstein, I.J.; McPhail, A.T. Tetrahedron Lett. 1993, 34, 4457. Porter, N.A.; Rosenstein, I.J. Tetrahedron Lett. 1993, 34, 7865.
25. For syntheses of related tetrahydrofuran derivatives, see: Udding, J.H.; Tuijp, K.J.M.; Van Zanden, M.N.A.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1994, 59, 1993. Burke, S.D.; Jung, K.W. Tetrahedron Lett. 1994, 35, 5837. Burke, S.D.; Jung, K.W.; Perry, R.E. Tetrahedron Lett. 1994, 35, 5841.
26. For syntheses of related tetrahydrofuran derivatives, see: Udding, J.H.; Tuijp, K.J.M.; Van Zanden, M.N.A.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1994, 59, 1993. Burke, S.D.; Jung, K.W. Tetrahedron Lett. 1994, 35, 5837. Burke, S.D.; Jung, K.W.; Perry, R.E. Tetrahedron Lett. 1994, 35, 5841.
27. For syntheses of related tetrahydrofuran derivatives, see: Udding, J.H.; Tuijp, K.J.M.; Van Zanden, M.N.A.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1994, 59, 1993. Burke, S.D.; Jung, K.W. Tetrahedron Lett. 1994, 35, 5837. Burke, S.D.; Jung, K.W.; Perry, R.E. Tetrahedron Lett. 1994, 35, 5841.