Silaketals in Intramolecular 1,3-Dipolar Cycloaddition of Nitrile Oxides

Synlett

Volumn 1997, Issue 10, 1997, Pages 1208-1210

  Dogbéavou, Romain ^a   Breau, Livain ^a  

^a UNIVERSITÉ DU QUÉBEC À MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343543429     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-991     Document Type: Article

References (17)

1. Gillard, J. W.; Fortin, R.; Grimm, E. L.; Maillard, M.; Tjepkema, M.; Bernstein, M. A.; Glaser, R., Tetrahedron Lett., 1991, 32, 1145-1148.
2. Shea K. J.; Zandi, K. S.; Staab, A.; Carr, R., Tetrahedron Lett., 1990, 31, 5885-5888.
3. Walkup, R. D.; Obeyesekere, N. U., J. Org. Chem., 1988, 53, 920-923. Journet, M.; Magnol, E.; Agnel, G.; Malacria, M., Tetrahedron Lett., 1990, 31, 4445.
4. Walkup, R. D.; Obeyesekere, N. U., J. Org. Chem., 1988, 53, 920-923. Journet, M.; Magnol, E.; Agnel, G.; Malacria, M., Tetrahedron Lett., 1990, 31, 4445.
5. Recently, silyloxinitroalkene has been used in the key step of an asymmetric tandem inter [4 + 2] / intra [3 + 2] cycloaddition. See Denmark, Scott E.; Hurd Alexander R. and Sacha H. J., J.Org. Chem, 1997, 62, 1668-1674. For an example of use of silicon tether in [3 + 2] dipolar cycloadditions of nitronates see Righi, P.; Marotta, E.; Laduzzi, A.; Rossi, G., J. Am. Chem. Soc., 1996, 118, 9446.
6. Recently, silyloxinitroalkene has been used in the key step of an asymmetric tandem inter [4 + 2] / intra [3 + 2] cycloaddition. See Denmark, Scott E.; Hurd Alexander R. and Sacha H. J., J.Org. Chem, 1997, 62, 1668-1674. For an example of use of silicon tether in [3 + 2] dipolar cycloadditions of nitronates see Righi, P.; Marotta, E.; Laduzzi, A.; Rossi, G., J. Am. Chem. Soc., 1996, 118, 9446.
7. Fairbanks, A.; Perrin, E.; Sinaÿ, P., Synlett, 1996, 679.
8. +, 19%); 207(34%); 191(16%); 133(49%); 73(100%). b) Typical procedure: one pot synthesis of nitrosilaketal 8a. To a cooled (-78°C) solution of dichlorodiphenylsilane (0.93 mL, 7.46 mmol, 1.0 equiv) in dry dichloromethane (15 mL) under nitrogen, dry triethylamine (1.04 mL, 7.46 mmol, 1.0 equiv) was added and the mixture was stirred for 5 min. A solution of cinnamyl alcohol (1.0g, 7.46 mmol, 1.0 equiv) in 10 mL of dry dichloromethane under nitrogen, was slowly added. After complete addition, the reaction was then allowed to warm slowly at room temperature. After stirring for 3 hours, the crude mixture was cooled again at -78°C. Triethylamine (1.04 mL, 7.46 mmol, 1.0 equiv), and a solution of 2-nitroethanol (0.5 mL, 7.5 mmol, 1.0 equiv) in 10 mL of dry dichloromethane was added. After one night period stirring at room temperature, the solvent was evaporated in vacuo. The residue was diluted with diethyl ether (30 mL) and the precipitate formed was removed by filtration and the filtrate was concentrated. Circular chromatography on silica gel with ethyl acetate/petroleum ether (1:5) gave the pure nitrosilaketal 8a (1.96 g, 65% yield).
9. Torsell, K. B. G., Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, VCH Weinhem, 1988.
10. Hutchinson, J. H.; Daynard, S. T.; Gillard, J. W., Tetrahedron Lett., 1991, 32, 573-576.
11. 1H NMR analysis of a sample of the crude reaction mixture showed a complete disappearance of the resonances attributed to the alkene function accompanied by the appearance of those attributed to the 2-isoxazoline product.
12. Mukaiyama, T.; Hoshino, T., J. Am. Chem. Soc., 1960, 82, 5339.
13. Bianchi, G.; De Micheli, C.; Gandolfi, R.; Grünanger, P.; Finzi, P. V.; De Pava, O. V., J. Chem. Soc., Perkin Trans. I, 1973, 148. Curran, D. P.; Heffner, T. A., J. Org. Chem., 1990, 55, 4585. Bast, K.; Christl, M.; Huisgen, R.; Mack, W., Chem. Ber., 1973, 106, 3312. For example, the intermolecular reaction of trans-cinnamyl alcohol with acetonitrile oxide, generated from nitroethane and phenylisocyanate under similar reaction conditions, gives a mixture of the corresponding 2-isoxazoline with poor regioselectivity (i.e. 1:1.2 ratio). (Equation Presented)
14. Bianchi, G.; De Micheli, C.; Gandolfi, R.; Grünanger, P.; Finzi, P. V.; De Pava, O. V., J. Chem. Soc., Perkin Trans. I, 1973, 148. Curran, D. P.; Heffner, T. A., J. Org. Chem., 1990, 55, 4585. Bast, K.; Christl, M.; Huisgen, R.; Mack, W., Chem. Ber., 1973, 106, 3312. For example, the intermolecular reaction of trans-cinnamyl alcohol with acetonitrile oxide, generated from nitroethane and phenylisocyanate under similar reaction conditions, gives a mixture of the corresponding 2-isoxazoline with poor regioselectivity (i.e. 1:1.2 ratio). (Equation Presented)
15. Bianchi, G.; De Micheli, C.; Gandolfi, R.; Grünanger, P.; Finzi, P. V.; De Pava, O. V., J. Chem. Soc., Perkin Trans. I, 1973, 148. Curran, D. P.; Heffner, T. A., J. Org. Chem., 1990, 55, 4585. Bast, K.; Christl, M.; Huisgen, R.; Mack, W., Chem. Ber., 1973, 106, 3312. For example, the intermolecular reaction of trans-cinnamyl alcohol with acetonitrile oxide, generated from nitroethane and phenylisocyanate under similar reaction conditions, gives a mixture of the corresponding 2-isoxazoline with poor regioselectivity (i.e. 1:1.2 ratio). (Equation Presented)
16. Kanemasa, S.; Nishiuchi, M.; Kamimura, A; Hori, K., J. Am Chem. Soc., 1994, 116, 2324-2339.
17. +, 9%); 147(16%); 133(15%); 73(100%).