A steric control of regioselectivity in palladium-catalyzed cyclizations of alkenes bearing arylbromides and nucleophiles

Tetrahedron Letters

Volumn 38, Issue 5, 1997, Pages 827-830

  Bruyère, Didier ^a   Gaignard, Gaelle ^a   Bouyssi, Didier ^a   Balme, Geneviève ^a   Lancelin, Jean Marc ^b  

^a CPE LYON   (France)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PHENANTHRENE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0038688823     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02442-2     Document Type: Article

References (18)

1. a.) Fournet, G. ; Balme, G.; Gore, J.; Van Hemelryck, B. Tetrahedron , 1990, 46, 7763-7774.
2. b) Balme, G. ; Bouyssi, D. ; Faure, R. ; Gore, J.; Van Hemelryck, B. Tetrahedron , 1992, 48, 3891-3902.
3. c) Bouyssi, D. ; Balme, G. ; Foumet, G.; Monteiro, N ; Gore, J.; Tetrahedron Lett. 1991, 32, 1641-1644.
4. Vittoz, P.; Bouyssi, D. ; Traversa, C. ; Goré , J.; Balme , G.; Tetrahedron Lett., 1994, 35, 1871-1874.
5. a) Balme, G. ; Bouyssi, D. Tetrahedron , 1994 , 50 ,403-414.
6. b) Cavicchioli, M. ; Bouyssi, D. ; Goré , J. ; Balme , G. ; Tetrahedron Lett. 1996, 37, 1429-1432,
7. c) Cavicchioli, M. ; Decortiat, S. ; Bouyssi, D. ; Goré , J. ; Balme , G. ; Tetrahedron 1996, 52, 11463-11478.
8. For a review on the Claisen Rearrangement see : Ziegler, F.E., Chem. Rev. 1988, 88, 1423-1450.
9. Cooke, M.P. and Widener R.K. J. Org. Chem., 1987, 52, 1381-139 . See also : Beak P. and Selling, G. W. J.Org.Chem. , 1989, 54, 5574-5580.
10. Cooke, M.P. and Widener R.K. J. Org. Chem., 1987, 52, 1381-139 . See also : Beak P. and Selling, G. W. J.Org.Chem. , 1989, 54, 5574-5580.
11. To our knowlege this aldehyde was not previously prepared using a Heck reaction . We used here the Jeffery's conditions ; Jeffery, T. Tetrahedron Lett., 1991, 32, 2121-2124.
12. 2 (0.05 mol.eq.) and dppe (0.05 mol.eq.) in the presence of 1-heptene ( 0.1eq., NMP, 50°C) until homogeneous dark red solution is obtained.
13. Full spcctroscopic data, consistent with the structures given, have been obtained for all compounds reported herein and the ratio of isomers was determined by capillary G.C. analysis.
14. J couplings were best measured on the ID after assigment from the 2D spectra.
15. Funk, R. L. and Vollhardt, K. P. C. J. Am. Chem. Soc. , 1980, 102, 5245-5253.
16. Substrate 1b was prepared by alkylation of methylmalonate with the mesylate derived from alcohol 5 and le by alkylation of malononitrile with the iodide derived from alcohol 5.
17. The difference in the rate of cyclization beetwen a malononitrile and a methylmalonate or a methylcyanoacetate derivative was already observed see : Bouyssi, D., Coudannc, I., Uriot, H., Goré J. and Balme G. Tetrahedron Lett. , 1995 , 36, 8019-8022.
18. 2),