Addition Reaction of Vinylic Reagents, Derived from α-Chloroenones, to Carbonyl Compounds Promoted by Samarium Diiodide

Chemistry - A European Journal

Volumn 9, Issue 21, 2003, Pages 5343-5347

  Concellón, José M ^a   Bernad, Pablo L ^a   Huerta, Mónica ^a   García Granda, Santiago ^a   Rosario Diaz M ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Baylis Hillman reaction; Diastereoselectivity; Nucleophilic addition; Samarium; Vinyl reagents

Indexed keywords

ACETONITRILE; ADDITION REACTIONS; ALDEHYDES; CHEMICAL BONDS; ISOMERS; KETONES; SAMARIUM COMPOUNDS;

CHEMICAL REAGENTS;

VINYL RESINS;

ACETONITRILE; ALDEHYDE DERIVATIVE; ALKYL GROUP; CARBONYL DERIVATIVE; CHLORINE DERIVATIVE; HYDROXYL GROUP; KETONE DERIVATIVE; REAGENT; SAMARIUM DIIODIDE; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; CONCENTRATION (PARAMETERS); DIASTEREOISOMER; MOLECULAR DYNAMICS; OXYGEN SATURATION; POWDER; STEREOCHEMISTRY;

EID: 0344065555     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304954     Document Type: Article

References (32)

1. a) P. G. Steel, J. Chem. Soc. Perkin Trans. 1 2001, 2727-2751;
2. b) J. A. Soderquist, Aldrichimica Acta 1991, 24, 15-23;
3. c) G. A. Molander, Chem. Rev. 1992, 92, 29-68;
4. d) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 92, 307-338;
5. e) G. A. Molander, C. R. Harris, Tetrahedron 1998, 54, 3321-3354;
6. f) A. Kief, A. M. Laval, Chem. Rev. 1999, 99, 745-777;
7. g) P. G. Steel, J. Chem. Soc. Perkin Trans. 1 2001, 2727-2751.
8. T. Skrydstrup, D. Mazéas, M. Elmouchir, G. Doisneau, C. Riche, A. Chiaroni, J.-M. Beau, Chem. Eur. J. 1997, 3, 1342-1356.
9. S. W. Youn, H. S. Park, Y. H. Kim, Chem. Commun. 2000, 2005-2006.
10. In other papers it has been argued that vinyl radicals in THF do not usually undergo further reduction to vinylsamarium reagents and readily abstract a hydrogen from solvents like THF, see ref. [1] and a) M. Kunishima, K. Hioki, S. Tani, A. Kato, Tetrahedron Lett. 1994, 35, 7253-7254;
11. b) L. Capella, P. C. Montevecchi, Tetrahedron Lett. 1994, 35, 8445-8448;
12. c) L. Capella, P. C. Montevecchi, M. L. Navacchia, J. Org. Chem. 1995, 60, 7424-7432.
13. a) C. M. Marson, J. H. Pink, C. Smith, Tetrahedron Lett. 1995, 36, 8107-8110;
14. b) P. Perlmutter, M. Tabone, J. Org. Chem. 1995, 60, 6515-6522;
15. c) Y. Génisson, C. Massardier, I. Gantier-Luneau, A. E. Greene, J. Chem. Soc. Perkin Trans. 1 1996, 2869-2872;
16. D. Basavaiah, M. Bakthadoss, S. Pandiaraju, Chem. Commun. 1998, 1639-1640.
17. To see reviews of the Baylis-Hillman reaction: a) S. E. Drewes, G. H. P. Roos, Tetrahedron 1988, 44, 4653-4670;
18. b) D. Basavaiah, P. D. Rao, R. S. Hyma, Tetrahedron 1996, 8001-8062.
19. G. Li, H.-X. Wei, S. Willis, Tetrahedron Lett. 1998, 39, 4607-4610.
20. a) J. S. Hill, N. S. Isaacs, Tetrahedron Lett. 1986, 27, 5007-5010;
21. b) J. S. Hill, N. S. Isaacs, J. Chem. Res. Synop. 1988, 330-331.
22. a) M. Kawamura, S. Kobayashi, Tetrahedron Lett. 1999, 40, 1539-1542;
23. b) J. N. Rosa, C. A. M. Afonso, A. G. Santos, Tetrahedron 2001, 57, 4189-4193.
24. a) Iodomethylation of α-aminoaldehydes: J. M. Concellón, P. L. Bernad, J. A. Pérez-Andrés, J. Org. Chem. 1997, 62, 8902-8906;
25. b) Diiodomethylation of carbonyl compounds: J. M. Concellón, P. L. Bernad, J. A. Pérez-Andrés, Tetrahedron Lett. 1998, 39, 1409-1412.
26. J. M. Concellón, M. Huerta, Tetrahedron 2002, 58, 7775-7780.
27. Although a real inversion of the stereochemistry of the C=C double bond take place, the nomenclature to designate the stereochemistry of 1 and 3 is Z in both cases.
28. 2 was prepared very rapidly (5 min) by sonication of a mixture of samarium powder and diiodomethane in THF: J. M. Concellón, H. Rodríguez-Solla, E. Bardales, M. Huerta, Eur. J. Org. Chem. 2003, 1775-1778.
29. When the reaction was carried out starting from aliphatic chloroenones instead of phenones 1, a complex mixture of products was obtained.
30. B. Hamann, J. L. Namy, H. Kagan, Tetrahedron 1996, 52, 14225-14234.
31. S. M. Ruder, Tetrahedron Lett. 1992, 33, 2621-2624.
32. CCDC-205964 (3i) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336033; or e-mail: deposit@ccdc.cam.ac.uk).