New nitrogenated siloxy butadienes from 1,3-dichloroacetone

Tetrahedron Letters

Volumn 48, Issue 6, 2007, Pages 907-910

  Alonso, Dulce ^a   Caballero, Esther ^a   Medarde, Manuel ^a   Tomé, Fernando ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

1,3 Dichloroacetone; 1 Formamido 1,3 butadienes; Diels Alder

Indexed keywords

1 FORMAMIDO 2 SILOXY 1,3 BUTADIENE; 1 FORMAMIDO 2 SILOXY 4 ARYL 1,3 BUTADIENE; 1,3 BUTADIENE DERIVATIVE; 1,3 DICHLOROACETONE; ACETONE; ALKADIENE; ALKALOID DERIVATIVE; PHOSPHORANE DERIVATIVE; POLYCYCLIC ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG SYNTHESIS; HORNER REACTION; METHODOLOGY; SILYLATION;

BETULACEAE;

EID: 33846072168     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.039     Document Type: Article

References (19)

1. Caballero E., Alonso D., Peláez R., Alvarez N., Puebla P., Sanz F., Medarde M., and Tomé F. Tetrahedron 61 (2005) 6871-6878
2. Caballero E., Alonso D., Peláez R., Alvarez C., Puebla P., Sanz F., Medarde M., and Tomé F. Tetrahedron Lett. 45 (2004) 1631-1634
3. Caballero E., Adeva M., Calderón S., Sahagún H., Tomé F., Medarde M., Fernández J.L., López-Lázaro M., and Ayuso M.J. Bioorg. Med. Chem. 11 (2003) 3413-3421
4. Acosta J.C., Caballero E., Grávalos D.G., Medarde M., Sahagún H., Stoodley R.J., and Tomé F. Bioorg. Med. Chem. Lett. 7 (1997) 2955-2958
5. Caballero E., Garci{dotless}́a F., Grávalos D.G., Medarde M., Sahagún H., and Tomé F. Bioorg. Med. Chem. Lett. 6 (1996) 2459-2462
6. Caballero E., Guilhot F., López J.L., Medarde M., Sahagún H., and Tomé F. Tetrahedron Lett. 37 (1996) 6951-6954
7. Alonso, D.; Álvarez, C; Gómez, R. G. (Degree research projects 2002-2003, unpublished results).
8. Yinglin H., and Hongwen H. Synthesis (1990) 122-124
9. Yinglin H., and Hongwen H. Tetrahedron Lett. 30 (1989) 5285-5286
10. Balo C., Blanco J.M., Fernández F., Lens E., and López C. Tetrahedron 54 (1998) 2833-2842
11. Flitsch W., Hampel K., and Hohenhorst M. Tetrahedron Lett. 28 (1987) 4395-4396
12. In diglyme a complex mixture was produced. After a careful scrutiny of the reaction conditions, 6 mol/mol of sodium diformylamide in DMF (Ref. 5) 30 min at 100 °C produced a 60% yield of 4. With longer periods of time or higher temperature, 3-hydroxypyrrol and triphenylphosphine oxide were obtained, from an internal Wittig reaction, as the major products.
13. 3).
14. Crystallographic data (excluding structure factors) for 9 and 10 are deposited at the Cambridge Crystallographic Data Centre as Supplementary data (CCDC 268250 and CCDC 200219, respectively).
15. Danishefsky S., Schuda P.F., Kitahara T., and Etheredge S.J. J. Am. Chem. Soc. 99 (1977) 6066-6075
16. 3).
17. A similar arrangement of functional groups has been reported to occur from dihydroxylation of silyl enol ethers. See, among others, the following references for further details:. Jauch J. Tetrahedron 50 (1994) 12903-12912
18. Zhu Y., Tu Y., Yu H., and Shi Y. Tetrahedron Lett. 39 (1998) 7819-7822
19. McCormick J.P., Tomasik W., and Johnson M.W. Tetrahedron Lett. 22 (1981) 607-610