Peterson allenation using (Z)-(1-lithio-1-alkenyl)trimethylsilanes

Synlett

Volumn , Issue 16, 2006, Pages 2577-2580

  Tsubouchi, Akira ^a   Kira, Takashiro ^a   Takeda, Takeshi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

Alcohols; Allenes; Carbonyl; Elimination; Silicon

Indexed keywords

ALLENE DERIVATIVE; CARBONYL DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ELIMINATION REACTION;

EID: 33750061055     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951474     Document Type: Article

References (19)

1. (a) Ager, D. J. Org. React. 1990, 38, 1.
2. (b) Kano, N.; Kawashima, T. In Modern Carbonyl Olefination; Takeda, T., Ed.; Wiley-VCH: Weinheim, 2004, 18.
3. Hudrlik, P. F.; Peterson, D. J. Am. Chem. Soc. 1975, 97, 1464.
4. Sato, F.; Tanaka, Y.; Sato, M. J. Chem. Soc., Chem. Commun. 1983, 165.
5. Wilson, S. R.; Georgiadis, G. M. J. Org. Chem. 1983, 48, 4143.
6. (a) Tius, M. A.; Pal, S. K. Tetrahedron Lett. 2001, 42, 2605.
7. (b) The transformation of disilanyl propargyl ethers to silylallenes, which is suggested to involve the Peterson elimination of lithium β-silylallylic alkoxides, has been reported: Suginome, M.; Matsumoto, A.; Ito, Y. J. Org. Chem. 1996, 61, 4884.
8. 4-(4H-pyranyl)[3]cumulenes by reaction of aromatic aldehydes and ketones with lithiated acetylenic pyranes has been reported: Doney, J. J.; Chen, C. H. Synthesis 1983, 491.
9. The lithium alkoxides of (Z)-β-silylallylic alcohols 6 can be prepared in ether, see: Chan, T. H.; Mychajlowskij, W.; Ong, B. S.; Harpp, D. N. J. Org. Chem. 1978, 43, 1526.
10. For the effect of solvent polarity on silyl migration, see: Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503.
11. 18: C, 92.26; H, 7.74. Found: C, 92.06; H, 8.02.
12. (a) Bratovanov, S.; Bienz, S. Main Group Met. Chem. 1996, 19, 769.
13. (b) Torres, E.; Larson, G. L.; McGarvey, G. J. Tetrahedron Lett. 1988, 29, 1355.
14. (c) Larson, G. L.; Torres, E.; Morales, C. B.; McGarvey, G. J. Organometallics 1986, 5, 2274.
15. 24: C, 92.54; H, 7.46. Found: C, 92.28; H, 7.59.
16. (1-Bromo-1-alkenyl)silanes 9 were prepared from alkynylsilanes by hydroalumination followed by treatment with bromine, see: Zweifel, G.; Lewis, W. J. Org. Chem. 1978, 43, 2739.
17. Zweifel, G.; Murray, R. E.; On, H. P. J. Org. Chem. 1981, 46, 1292.
18. 9a gave 2a in 8% yield and the protodesilylation product, 1-phenyl-4-undecen-3-ol, was isolated in 66% yield. The Peterson elimination of 1a in the presence of lithium iodide gave 2a in only 18% yield. Decrease of the yield might, therefore, be attributable to iodide ion generated by the lithium-halogen exchange.
19. Shono, T.; Itoh, K.; Tsubouchi, A.; Takeda, T. Org. Biomol. Chem. 2005, 3, 2914.