Sulfoxide-controlled S(N)2' displacements between cyanocuprates and epoxy vinyl sulfoxides

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 8031-8034

  Marino, Joseph P ^a   Anna, Laura J ^a   Fernández De La Pradilla, Roberto ^b   Martínez, María Victoria ^b   Montero, Carlos ^b   Viso, Alma ^c  

^a UNIVERSITY OF MICHIGAN   (United States)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^c UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030605105     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01817-5     Document Type: Article

References (28)

1. 1. Taken in part from the M.S. Thesis of M. V.M. and Ph.D. Theses of L.J.A. and C.M. Presented, in part, at the 6th Brazilian Meeting on Organic Synthesis, Sao Paulo, September 5-9, 1994.
2. 3. For reviews see: (a) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631.
3. (b) Marshall, J. A. Chem Rev. 1989, 89, 1503-1511.
4. 4. (a) Nagumo, S.; Irie, S.; Akita, H. J. Chem. Soc., Chem. Commun. 1995, 2001-2002.
5. (b) Clive, D. L. J.; Wickens, P. L.; da Silva, G. V. J. J. Org. Chem. 1995, 60, 5532-5536.
6. N2′ displacements on vinyl aziridines, see:
7. (d) Fujii, N.; Nakai, K.; Tamamura, H.; Ibuka, T. J. Chem Soc. Perkin Trans. 1 1995, 1359-1371.
8. (e) Wipf, P.; Frich, P. C. J. Org. Chem. 1994, 59, 4875-4886.
9. 5. (a) Arjona, O.; Fernández de la Pradilla, R.; Mallo, A.; Plumet, J.; Viso, A. Tetrahedron Lett. 1990, 31, 1475-1478.
10. (b) Marino, J. P.; Viso, A.; Fernández de la Pradilla, R.; Fernández, P. J. Org. Chem. 1991, 56, 1349-1351.
11. (c) Marino, J. P.; de Dios, A.; Anna, L. J.; Fernández de la Pradilla, R. J. Org. Chem. 1996, 61, 109-117.
12. 6. (a) Posner, G. H.; Tang, P.W.; Mallamo, J. P. Tetrahedron Lett. 1978, 3995-3998.
13. (b) Okamura, H.; Mitsuhira, Y.; Miura, M.; Takei, H. Chem Lett. 1978, 517-520.
14. 7. Stevens, C. L.; Farkans, E.; Gillis, B. J. Am. Chem. Soc. 1954, 76, 2695-2698.
15. 8. Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5180-5182.
16. 9. All new products reported here have been fully characterized and yields are based on purified compounds obtained by unoptimized procedures. The relative configuration of epoxide 12 was secured by an X-ray diffraction analysis of the chlorohydrin precursor. These results will be described in detail in a full account of this research.
17. 10. (a) Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017-3020.
18. For reviews, see: (a) Hughes, D. L. Org. React. 1992, 42, 335-669.
19. (b) Hughes, D. L. Org. Prep. and Proc. Int. 1996, 28, 127-164.
20. N2′ displacements involving organocopper reagents and vinyl oxiranes are scarce and generally involve special substrates or organocopper reagents. See: (a) Hudlicky, T.; Tian, X.; Königsberger, K.; Rouden, J. J. Org. Chem. 1994, 59, 4037-4039.
21. (b) Marshall, J. A.; Sedrani, R. J. Org. Chem. 1991, 56, 5496-5498.
22. (c) Marshall, J. A.; Audia, V. H. J. Org. Chem. 1987, 52, 1106-1113.
23. (d) Marino, J. P.; Fernández de la Pradilla, R.; Laborde, E. J. Org. Chem. 1987, 52, 4898-4913.
24. N2'′ displacement on a cyclic epoxy vinyl sulfone with MeLi, see: Saddler, J. C.; Fuchs, P. L. J. Am. Chem. Soc. 1981, 103, 2112-2114.
25. N2'′ displacement on a cyclic epoxy vinyl sulfone with MeLi, see: Saddler, J. C.; Fuchs, P. L. J. Am. Chem. Soc. 1981, 103, 2112-2114.
26. 12. For leading references see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
27. (b) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968.
28. 13. For the sulfur-directed nucleophilic epoxidation of allylic hydroxy vinyl sulfoxide derivatives, see: Fernández de la Pradilla, R.; Manzano, P.; Priego, J. Viso, A.; Martínez-Ripoll, M.; Rodríguez, A., Tetrahedron Lett. 1996, in press.