Stereoselective formation of cyclopropylsilane through intramolecular rearrangement of [(Allyloxy)dimesitylsilyl]lithiums

Chemistry Letters

Volumn , Issue 10, 2000, Pages 1216-1217

  Kawachi, Atsushi ^a   Maeda, Hirofumi ^a   Tamao, Kohei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034335955     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.1216     Document Type: Article

References (22)

1. a) A. Kawachi, N. Doi, and K. Tamao, J. Am. Chem. Soc., 119, 233 (1997).
2. b) A. Kawachi and K. Tamao, Bull. Chem. Soc. Jpn., 70 945 (1997).
3. The term "tert-allyl" means that the allylic carbon is tertiary. The term "sec-allyl" is used in a similar way in this paper.
4. Recent allylsilane synthesis: e.g., a) M. Suginome, A. Matsumoto, and Y. Ito, J. Am. Chem. Soc., 118, 3061 (1996).
5. b) J. H. Smitrovich and K. A. Woerpel, J. Org. Chem., 65, 1601 (2000).
6. The mesityl groups on the silicon are introduced to prevent the attack of n-BuLi on the silicon center.
7. The silylstannane 1 was prepared by the reaction of the (E)-and (Z)-4-phenyl-3-buten-2-ols and [(chloro)dimesitylsilyl]-trimethylstannane in THF in the presence of triethylamine and pyridine in a manner similar to the procedure reported in Ref. 1a.
8. 34OSi: C, 81.10; H, 8.26%. Found: C, 81.04; H, 8.49%.
9. w = 0.083. The crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (No. CCDC-147730).
10. Nomenclature of cyclic compounds: E. L. Eliel and S. H. Wilen, in "Stereochemistry of Organic Compounds," John Wiley & Sons Inc New York (1994), Chap. 11.
11. Formation of oxasilacyclobutanes, e.g.: K. Tamao, Y. Nakagawa, and Y. Ito, Organometallics, 12, 2297 (1993). See also Ref. 3a.
12. Cyclopropane synthesis by intramolecular cyclization of organolilhium compounds: a) A. Krief and M. Hohe, Tetrahedron Lett., 33, 6529 (1992).
13. b) D. Hoppe, M. Paetow, and F. Hintze, Angew. Chem., Int. Ed. Engl., 32, 394 (1993).
14. c) S. Norsikian, I. Marek, J-F. Poisson, and J. F. Normant, J. Org. Chem., 62, 4898 (1997).
15. d) D. Cheng, K. R. Knox, and T. Cohen, J. Am. Chem. Soc., 122, 412 (2000).
16. Reviews for cyclopropane synthesis: a) J. Salaün, Chem. Rev., 89, 1247 (1989).
17. b) A. Pfaltz, Acc. Chem. Res., 26, 339 (1993).
18. c) A. B. Charette and J-F. Marcoux, Synlett, 1195, 1197.
19. A silylcuprate adds to allenes in a syn fashion: F. J. Blanco, P. Cuadrado, A. M. González, and F. J. Pulido, Tetrahedron Lett., 35, 8881 (1994).
20. R. E. Gawley, E. Low, Q. Zhang, and R. Harris, J. Am. Chem Soc 122, 3344 (2000), and references cited therein.
21. All calculations were performed with the Gaussian 94 program package.
22. The nature of the nucleophile, the silyllithium moiety, may be also an important factor for this reaction mode, considering that the carbon analog derived from cinnamyl methyl ether underwent the [2,3]-Wittig rearrangement: M. P. Doyle, V. Bagheri, and N. K. Harn, Tetrahedron Lett., 29, 5119 (1988).