Mercuri-desilylation of chiral cyclopropylmethylsilanes

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1209-1212

  Landais, Yannick ^a   Parra Rapado, Liliana ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030039955     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02387-9     Document Type: Article

References (26)

1. Landais, Y.; Parra-Rapado, L. Tetrahedron Lett., preceding communication.
2. Carey, F.A.; Sundberg, R.J. in "Advanced Organic Chemistry", 3rd Edition, Plenum : New-York, 1991, part A, p. 157.
3. (a) Mohr, P. Tetrahedron Lett., 1995, 36, 7221-7224;
4. (b) Fleming, I.; Sanderson, P.E.J.; Terrett, N.K. Synthesis, 1992, 69-74;
5. (c) Panek, J.S.; Garbaccio, R.M.; Jain, N.F. Tetrahedron Lett., 1994, 35, 6453-6456.
6. (a) Ryu, I.; Suzuki, H.; Murai, S.; Sonoda, N. Organometallics, 1987, 6, 212-213;
7. (b) Grignon-Dubois, M.; Dunoguès, J.; Calas, R. Tetrahedron Lett., 1981, 22, 2883-2884;
8. (c) Ryu, I.; Hirai, A.; Suzuki, H.; Sonoda, N.; Murai, S. J. Org. Chem., 1990, 55, 1409-1410;
9. (d) Kihihara, M.; Yokoyama, S.; Kakuda, H.; Momose, T. Tetrahedron Lett., 1995, 36, 6907-6910.
10. (a) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc., 1994, 116, 186-197;
11. (b) Kocovsky, P.; Pour, M.; Gogoll, A.; Hanus, V.; Smrcina, M. J. Am. Chem. Soc., 1990, 112, 6735-6737.
12. Lambert, J.B.; Schulz, W.J.; Mueller, P.H.; Kobayashi, K. J. Am. Chem. Soc., 1984, 106, 792-793.
13. 4 led to a complex mixture of products.
14. Collum, D.B.; Mohamadi, F.; Hallock, J.S. J. Am. Chem. Soc., 1983, 105, 6882-6889.
15. 2 in the same solvent gave only recovered starting material.
16. (a) White, J.M. Aust. J. Chem., 1995, 48, 1227-1251;
17. (b) Lambert, J.B. Tetrahedron, 1990, 46, 2677-2689.
18. Roush, W.R.; Grover, P.T. Tetrahedron, 1992, 48, 1981-1998 and references cited therein.
19. (a) Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett., 1995, 36, 2987-2990;
20. (b) Landais, Y.; Planchenault, D. Synlett, 1995, 1191-1193. It is still premature to make conclusions about the exact conformation at the transition state in this 5-endo-trig cyclization.
21. Fleming, I.; Lawrence, N.J.; Sarkar, A.K.; Thomas, A.P. J. Chem. Soc., Perkin Trans 1, 1992, 3303-3308.
22. Nishimura, J.; Kawabata, N.; Furukawa, J. Tetrahedron, 1969, 25, 2647-2659.
23. The C-Si bond oxidation proceeds with retention of configuration at the carbon centre, see : (a) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics, 1983, 2, 1694-1696;
24. (b) Tamao, K.; Ishida, N. Tetrahedron Lett., 1984, 25, 4245-4248;
25. (c) Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron, 1983, 39, 983-990;
26. (d) Fleming, I.; Henning, R.; Parker, D.C.; Plaut, H.E.; Sanderson, P.E.J. J. Chem. Soc., Perkin Trans 1, 1995, 317-337.