References and Notes


  1. (a) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics, 1983, 2, 1694-1696; (b) Tamao, K.; Ishida, N. Tetrahedron Lett., 1984, 25, 4245-4248; (c) Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron, 1983, 39, 983-990.

  2. Fleming, I.; Henning, R.; Parker, D.C.; Plaut, H.E.; Sanderson, P.E.J. J. Chem. Soc., Perkin Trans 1, 1995, 317- 337 and references cited therein.

  3. For miscellaneous silicon groups used in the C-Si bond oxidation, see: (a) Aminomethylsilyl : Chan, T.H.; Nwe, K.T. J. Org. Chem., 1992, 57, 6107-6111; (b) Allyldimethylsilyl : Tamao, K.; Ishida, N. Tetrahedron Lett., 1984, 25, 4249-4252; Magar, S.S.; Fuchs, P.L. Tetrahedron Lett., 1991, 32, 7513-7516; Magar, S.S.; Desai, R.C.; Fuchs, P.L. J. Org. Chem., 1992, 57, 5360-5369; (c) Furyldimethylsilyl : Stork, G. Pure & Appl. Chem. 1989, 61, 439- 442; (d) 5-Methylthienyldimethylsilyl : Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett., 1995, 36, 2987-2990; (e) Me3Si-SiMe2- : Krohn, K.; Khanbabaee, K. Angew. Chem. Int. Ed. Engl., 1994, 33, 99-100.

  4. For some applications in total synthesis: (a) Chow, H.F.; Fleming, I. Tetrahedron Lett., 1985, 26, 397-400; (b) Fleming, I.; Kilburn, J.D., J. Chem. Soc., Chem. Commun., 1986, 1198-1199; (c) Dener, J.M.; Hart, D.J. Tetrahedron, 1988, 44, 7037-7046; (d) Overman, L.E.; Wild, H. Tetrahedron lett., 1989, 30, 647-650; (e) O'Brien, M.K.; Pearson, A.J.; Pinkerton, A.A.; Schmidt, W.; Willman, K. J. Am. Chem. Soc., 1989, 111, 1499-1501; (f) Fleming, I.; Armstrong, S.K.; Pollitt, R.J. J. Chem. Res.(S), 1989, 19-19; (g) Koreeda, M.; Teng, K.; Murata, T. Tetrahedron Lett., 1991, 31, 5997-6000; (h) Fleming, I.; Lawrence, N.J. Tetrahedron Lett., 1990, 31, 3645-3648; (i) Boons, G.J.P.H.; van der Marel, G.A.; van Boom, J.H. Tetrahedron lett., 1990, 30, 229-232; (j) Kolb, H.C.; Ley, S.V.; Slawin, A.M.Z.; Williams, D.J. J. Chem. Soc., Perkin Trans 1, 1992, 2735-2762; (k) Polniaszek, R.P.; Dillard, L.W. J. Org. Chem., 1992, 57, 4103-4110.

  5. (a) Fleming, I.; Winter, S.B.D. Tetrahedron Lett., 1993, 34, 7287-7290; (b) Norley, M.C.; Kocienski, P.J.; Faller, A. Synlett, 1994, 77-78; (c) Taber, D.F.; Yet, L.; Bhamidipati, R.S. Tetrahedron Lett., 1995, 36, 351-354; (d) Hunt, J.A.; Roush, W.R. Tetrahedron Lett., 1995, 36, 501-504.

  6. Oae, S.; Numata, T. "The Pummerer type of reactions" in Isotopes in Organic Synthesis; Buncel, E.; Lee, C.C. Eds.; Elsevier: New-York, 1980; vol. 5, chap. 2.

  7. Tanaka, K.; Uneme, H.; Matsui, S.; Tanikaga, R.; Kaji, A. Chem. Lett., 1980, 287-288.

  8. Bhupathy, M.; Cohen, T. Tetrahedron Lett., 1987, 28, 4793-4796.

  9. For a review on superbases, see: Schlosser, M. "Organoalkali reagents" in Organometallics in Synthesis; Schlosser, M. Ed.; John Wiley and sons, Inc.: Chichester, 1994; pp. 1-166.

  10. (a) Chan, T.H.; Labrecque, D. Tetrahedron Lett., 1992, 33, 7997-8000; (b) Li, L.-H.; Wang, D.; Chan, T.H. Tetrahedron Lett., 1991, 32, 2879-2882; (c) Tamao, K.; Nakajo, E.; Ito, Y. Synth. Commun., 1987, 17, 1637-1646.

  11. Oxidation is usually carried out using m-CPBA. However, milder conditions, compatible with double bonds and electrophile-sensitive functionalities, are available using BuOH-H2O2-V2O5(cat.). For the preparation, the scope and limitations of this reagent, see : Miklos, P.; Senning, A. Tetrahedron, 1987, 43, 249-254.

  12. Fuchs recently showed that PhSO2R groups are excellent nucleofugal groups on silicon [3b].

  13. Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett., 1994, 35, 9549-9552.

  14. (a) Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Pure & Appl. Chem. 1994, 94, 2483-2547; (b) Bassindale, A.R.; Taylor, P.G.; Xu, Y.L. J. Chem. Soc. Perkin Trans 1, 1994, 1061-1067.

  15. Fuganti, C.; Grasselli, P.; Servi, S.; Lazzarini, A.; Casati, P. Tetrahedron, 1988, 44, 2575-2582.

  16. Abd. Rahman, N.; Fleming, I. Synth. Commun., 1993, 23, 1583-1594.

  17. (a) Maruoka, K.; Fukutani, Y.; Yamamoto, H. J. Org. Chem., 1985, 50, 4412-4414; (b) Morikawa, T.; Sasaki, H.; Hanai, R.; Shibuya, A.; Taguchi, T. J. Org. Chem., 1994, 59, 97-103.

  18. We observed that this cyclopropanation was difficult to reproduce. For a report concerning the failure of Simmons-Smith reactions in the presence of thioether, see : Kosarych, Z.; Cohen, T. Tetrahedron Lett., 1982, 23, 3019-3022.

  19. Direct oxidation using the classical Tamao conditions afforded a complex mixture. It is likely that displacement of the cyclopropylsulfone moiety in 22 is difficult due to steric hindrance around silicon.

  20. It is worthy of note that the m-CPBA oxidation gave only 55% yield after purification, the cyclopropanation-C-Si oxidation (3 steps) giving 57% overall yield.