The Trimethylsilyl Cationic Species as a Bulky Proton. Application to Chemoselective Dioxolanation

Journal of Organic Chemistry

Volumn 50, Issue 20, 1985, Pages 3946-3948

  Hwu, Jih Ru ^a   Wetzel, John M ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001013179     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00220a062     Document Type: Article

References (11)

1. Fleming, I. Chem. Soc. Rev. 1981, 10, 83.
2. For recent reviews and books, see: (a) Ager, D. J. Synthesis 1984, 384. (b) Weber, W. P. “Silicon Reagents for Organic Synthesis;” Springer-Verlag: New York, 1983. (c) Colvin, E. W. “Silicon in Organic Synthesis;” Butterworths: Boston, 1981. (d) Chan, T. H.; Fleming, I. Synthesis 1979, 761.
3. (a) Greene, T. W. “Protective Groups in Organic Synthesis;” John Wiley and Sons: New York, 1981; p 116. (b) Loewenthal, H. J. E. “Protective Groups in Organic Chemistry;” McOmie, J. F. W., Ed.; Plenum Press: New York, 1973; p 323.
4. (a) Noyori, R.; Murata, S.; Suzuki, M. Tetrahedron 1981, 37, 3899. (b) Marsmann, H. C.; Horn, H.-G. Z. Naturforsch. B 1972, 27, 1448.
5. For reviews, see: (a) Stang, P. J.; White, M. R. Aldrichimica Acta 1983, 16, 15. (b) Emde, H.; Domsch, D.; Feger, H.; Frick, U.; Gotz, A.; Hergott, H. H.; Hofmann, K.; Kober, W.; Krageloh, K.; Oesterle, T.; Steppan, W.; West, W.; Simchen, G. Synthesis 1982, 1.
6. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
7. Vorbrüggen, H. Steroids 1963, 1, 45. Nitz, T. J.; Paquette, L. A. Tetrahedron Lett. 1984, 25, 3047 and references therein.
8. (a) Herzog, H. L.; Jevnik, M. A.; Tully, M. E.; Hershberg, E. B. J. Am. Chem. Soc. 1953, 75, 4425. (b) De Leeuw, J. W.; De Waard, E. R.; Beetz, T.; Huisman, H. 0. Reel. Trav. Chim. Pays-Bas 1973, 92, 1047.
9. 3) of 9: δ 5.23 (br s, 1 H), 3.97 (m, 4 H), 2.11 (s, 3 H), 2.67-0.74 (m, 20 H), 1.03 (s, 3 H), 0.63 (s, 3 H).
10. 3) of 14: δ 5.96 (dt, J = 15.3, 6.0 Hz, 1 H), 5.49 (dd, J = 15.3, 6.0 Hz, 1 H), 5.17 (d, J = 6.0 Hz, 1 H), 3.93 (m, 4 H), 2.70-2.10 (m, 4 H), 1.13 (s, 9 H).
11. 2 at -78 °C for 78 h gave 19 as the only monodioxolane product (68%), along with diketal 20 (30%). (a) Barton, D. H. R.; Head, A. J.; May, P. J. J. Chem. Soc. 1957, 935. (b) Eliel, E. L.; Allinger, N. L.; Angyal, S. J.; Morrison, G. A. “Conformational Analysis;” Interscience; reprinted by the American Chemical Society: Washington, DC, 1981; p 345.