TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes

Tetrahedron Letters

Volumn 46, Issue 35, 2005, Pages 5803-5806

  Anastasia, Luigi ^a   Giannini, Elios ^a   Zanoni, Giuseppe ^a   Vidari, Giovanni ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

Aldehydes; Allylsilane; Biomimetic reactions; Cyclization; TiF4

Indexed keywords

ALDEHYDE; ALKADIENE; FLUORINE; LEWIS ACID; TITANIUM;

ALKYLATION; ARTICLE; BIOMIMETICS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SUBSTITUTION REACTION;

EID: 23044486560     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.149     Document Type: Article

References (23)

1. G. Vidari, and P. Vita Finzi Tetrahedron 47 1991 7109 7116
2. M. De Bernardi, L. Garlaschelli, G. Gatti, G. Vidari, and P. Vita Finzi Tetrahedron 44 1988 235 240
3. K. Yoshikawa, M. Kuroboshi, S. Arihara, N. Miura, N. Tujimura, and K. Sakamoto Chem. Pharm. Bull. 50 2002 1603 1606
4. D.-A. Sun, J.-Z. Deng, R.S. Starck, and S.M. Hecht J. Am. Chem. Soc. 121 1999 6120 6124
5. T. Takahashi, H. Iwamoto, K. Nagashima, T. Okabe, and T. Doi Angew. Chem., Int. Ed. Engl. 36 1977 1319 1321
6. J.P. Férézou, and M. Julia Tetrahedron 46 1990 475 486
7. M. Julia, and C. Schmitz Tetrahedron 42 1986 2491 2500
8. T. Kumagai, F. Ise, T. Uyehara, and T. Kato Chem. Lett. 1981 25 28
9. T. Kato, H. Takayanagi, T. Suzuki, and T. Uyehara Tetrahedron Lett. 19 1978 1201 1204
10. S. Kumazawa, Y. Nakano, T. Kato, and Y. Kitahara Tetrahedron Lett. 15 1974 1757 1760
11. W.A. Smit, A. Semenovsky, V.F. Kucherov, T.N. Chernova, M.Z. Krimer, and O.V. Lubinskaya Tetrahedron Lett. 12 1971 3101 3106 and references therein
12. G. Vidari, M.P. Bonvicelli, L. Anastasia, and G. Zanoni Tetrahedron Lett. 41 2000 3471 3474
13. 4 in the enantioselective addition of allyltrimethylsilane to aldehydes, see: D.R. Gauthier Jr., and E.M. Carreira Angew. Chem., Int. Ed. 35 1996 2363 2365
14. S. Beszant, E. Giannini, G. Zanoni, and G. Vidari Tetrahedron: Asymmetry 13 2002 1245 1255
15. R.J. Armstrong, and L. Weiler Can. J. Chem. 64 1986 584 596
16. R.J. Armstrong, and L. Weiler Can. J. Chem. 61 1983 214 215
17. 2 = Et or Pr).
18. 2 calcd: C, 76.23; H, 10.24. Found: C, 76.38; H, 10.32.
19. M.G. Organ, D.D. Winkle, and J. Huffmann J. Org. Chem. 62 1997 5254 5266
20. S.E. Denmark, and N.G. Almstead Modern Carbonyl Chemistry J. Otera Allylation of Carbonyls: Methodology and Stereochemistry 2000 Wiley-VCH Weinheim (FDR) 299 401
21. 10 leading to 6a, the R group would develop an unfavorable allylic strain with the pseudoequatorial methyl group on the distal double bond of diene 2.
22. I. Fleming, and A. Pearce J. Chem. Soc., Perkin Trans. 1 1981 251 255
23. 2Me) appears to be activated by the allylsilyl group in the same manner as in 1,3-dienylsilanes; see: I. Fleming, N.D. Kindon, and A.K. Sarkar Tetrahedron Lett. 28 1987 5921 5924 and references cited therein