Double nucleophilic addition of bis(trimethylsilyl)ketene acetals to carbon-carbon double bonds of pyrazines: Formation of polycyclic γ-lactones

Tetrahedron Letters

Volumn 46, Issue 20, 2005, Pages 3449-3451

  Rudler, Henri ^a   Denise, Bernard ^a   Xu, Yiming ^a   Vaissermann, Jacqueline ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Ketene acetals; Lactones; Pyrazines

Indexed keywords

1,1,1 TRICHLOROETHANE; ACETAL DERIVATIVE; CARBON; GAMMA LACTONE DERIVATIVE; OXYGEN; PYRAZINE; SILICON;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 17844405033     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.131     Document Type: Article

References (20)

1. J.P. Collman, L.S. Hegedus, J.R. Norton, and R.G. Fincke Principles and Applications of Organotransition Metal Chemistry 2nd ed. 1987 University Science Books Mill Valley, CA
2. M.F. Semmelhack E.W. Abel Comprehensive Organometallic Chemistry II Vol. 12, Chapters 9.1 and 9.2 1995 Pergamon Oxford, UK p 979
3. F.J. McQuillin, D.G. Parker, and G.R. Stephenson Transition Metal Organometallics for Organic Synthesis 1991 Cambridge University Press Cambridge, UK
4. S.C. Meiere, M.T. Valahovic, and W.D. Harman J. Am. Chem. Soc. 124 2002 15099
5. A.J. Pearson, Md.N.I. Khan, J.C. Clardy, and H. Cun-Heng J. Am. Chem. Soc. 107 1985 2748
6. A.R. Pape, K.P. Kalapian, and E.P. Kündig Chem. Rev. 100 2000 2917
7. H. Rudler, V. Comte, E. Garrier, M. Bellassoued, E. Chelain, and J. Vaissermann J. Organomet. Chem. 621 2001 284
8. M. Bellassoued, E. Chelain, J. Collot, H. Rudler, and J. Vaissermann J. Chem. Soc., Chem. Commun. 1999 187
9. Similar results were observed in the case of cycloheptatrienechromium tricarbonyl complexes, see: H. Rudler, C. Alvarez, E. Aldeco-Perez, B. Denise, Y. Xu, and J. Vaissermann Tetrahedron Lett. 45 2004 2409
10. For an excellent recent review, see: R. Lavilla J. Chem. Soc., Perkin Trans. 1 2002 1141 and references cited therein
11. T. Itoh, M. Miyazaki, K. Nagata, and A. Ohsawa Heterocycles 46 1997 83
12. T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya, M. Okada, and A. Oshawa Chem. Pharm. Bull. 42 1994 1768
13. For an earlier example, see: S. Raussou, R. Gosmini, P. Mangeney, A. Alexakis, and M. Commerçon Tetrahedron Lett. 32 1991 3981
14. H. Rudler, B. Denise, A. Parlier, and J.C. Daran Chem. Commun. 2002 940
15. K.-y. Akiba, Y. Nishihara, and M. Wada Tetrahedron Lett. 24 1983 5269
16. M. Bellassoued, R. Ennigrou, and M.J. Gaudemar J. Organomet. Chem. 338 1988 149
17. I. Fleming, J. Goldhill, and I. Paterson Tetrahedron Lett. 34 1979 3209
18. G. Bluet, and J.-M. Campagne J. Org. Chem. 66 2001 4293
19. T. Tokuyasu, and H. Mayr Eur. J. Org. Chem. 2004 2791
20. Experimental procedure: a dichloromethane solution (5 mL) of methylchloroformate (6 mmol) was added to a solution of bis(trimethylsilyl) ketene acetal (2.3 mmol) and pyrazine (2 mmol), at room temperature. Stirring for 1 h followed by evaporation of the solvent and chromatography (PE/AcOEt) on silica gel gave the products 4