Stereoconservative protodesilylation of substituted silyl dithianes

Tetrahedron Letters

Volumn 47, Issue 43, 2006, Pages 7525-7528

  Cerè, Vanda ^a   Capperucci, Antonella ^b   Degl'Innocenti, Alessandro ^b   Pollicino, Salvatore ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b Dipartimento di Chimica Organica   (Italy)

Author keywords

Desilylation; Fluoride ion; Silyldithianes; Stereocontrol

Indexed keywords

PHENYL GROUP; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; EPIMERIZATION;

EID: 33748755361     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.078     Document Type: Article

References (37)

1. Seebach D. Synthesis (1969) 17
2. Seebach D., and Corey E.J. J. Org. Chem. 40 (1975) 231
3. Bulman Page P.C., van Niel M.B., and Prodger J.C. Tetrahedron 45 (1989) 7643
4. Oida T., Tanimoto S., Terao H., and Okano M. J. Chem. Soc., Perkin Trans. 1 (1986) 1715
5. Wilson S.R., Georgiadis G.M., Khatri H.N., and Bartmess J.E. J. Am. Chem. Soc. 102 (1980) 3577
6. Wilson S.R., Caldera P., and Jester M.A. J. Org. Chem. 47 (1982) 3319
7. Capperucci A., Ferrara M.C., Degl'Innocenti A., Bonini B.F., Mazzanti G., Zani P., and Ricci A. Synlett (1992) 880
8. Capperucci A., Degl'Innocenti A., Leriverend C., and Metzner P. J. Org. Chem. 6 (1996) 7174
9. Degl'Innocenti A., and Capperucci A. Eur. J. Org. Chem. (2000) 2171 and references cited therein
10. Cerè V., Peri F., and Pollicino S. Heterocycles 51 (1999) 1025
11. Carini S., Cerè V., Peri F., and Pollicino S. Synthesis (2000) 1756
12. Capperucci A., Degl'Innocenti A., and Nocentini T. Tetrahedron Lett. 42 (2001) 4557
13. Capperucci A., Cerè V., Degl'Innocenti A., Nocentini T., and Pollicino S. Synlett (2002) 1447
14. Denmark S.E., and Almstead N.G. J. Org. Chem. 59 (1994) 5130
15. Corriu R. Pure Appl. Chem. 60 (1988) 99
16. Chan T.H., and Fleming I. Synthesis (1979) 761
17. Dubuffet T., Sauvetre R., and Normant J.F. Tetrahedron Lett. 29 (1988) 5923
18. Palmer W.S., and Woerpel K.A. Organometallics 16 (1997) 1097
19. Shaw J.T., and Woerpel K.A. J. Org. Chem. 62 (1997) 442
20. Bodnar P.M., Palmer W.S., Shaw J.T., Smitrovich J.H., Sonnenberg J.D., Presley A.L., and Woerpel K.A. J. Am. Chem. Soc. 117 (1995) 10575 and references cited therein
21. Hatanaka T., and Hiyama T. J. Am. Chem. Soc. 112 (1990) 7793
22. Corey E.J., and Chen Z. Tetrahedron Lett. 35 (1994) 8731
23. McDougall P., and Condon B.D. Tetrahedron Lett. 30 (1989) 789
24. Thayumanavan S., Park Y.S., Farid P., and Beak P. Tetrahedron Lett. 38 (1997) 5429
25. Aggarwal V.K., and Ferrara M. Org. Lett. 2 (2000) 4107
26. See Chan T.H., Lau P.W.K., and Li M.P. Tetrahedron Lett. (1976) 2667
27. Hartmann A.A., and Eliel E.L. J. Am. Chem. Soc. 93 (1971) 2572
28. Eliel E., Abatjoglou A.G., and Hartmann A.A. J. Am. Chem. Soc. 94 (1972) 4786
29. Eliel E.L. Angew. Chem., Int. Ed. Engl. 11 (1972) 739
30. Eliel E.L., Hartmann A.A., and Abatjoglou A.G. J. Am. Chem. Soc. 96 (1974) 1807
31. Eliel E.L. Tetrahedron 30 (1974) 1503
32. Abatjoglou A.G., Eliel E.L., and Kuyper L.F. J. Am. Chem. Soc. 99 (1977) 8262
33. Krief A., and Defrere L. Tetrahedron Lett. 37 (1996) 2667
34. Krief A., and Defrere L. Tetrahedron Lett. 37 (1996) 8011
35. Krief A., and Defrere L. Tetrahedron Lett. 37 (1996) 8015
36. 16d
37. Xie L., Bors D.A., and Streitweiser A. J. Org. Chem. 57 (1992) 4986