LiClO4 Mediated Substitution of β-Phenylsulfonyl-γ-oxo Arenebutanenitriles by Organomagnesium Reagents

Synlett

Volumn 1996, Issue 10, 1996, Pages 1001-1003

  Giovannini, Riccardo ^a   Petrini, Marino ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002870473     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5640     Document Type: Article

References (36)

1. a) Simpkins, N. S. in Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993;
2. b) Trost, B. M. Bull. Chem. Soc. Jpn 1988, 61, 107;
3. c) Magnus, P. D. Tetrahedron, 1977, 33, 2019.
4. a) Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 3477;
5. b) Marshall, J. A.; Cleary, D. G. J. Org. Chem. 1986, 51, 858;
6. c) Lee, G. H.; Choi, E. B.; Lee, E.; Pak, C. S. Tetrahedron Lett. 1993, 34, 4541;
7. d) Corey, E. J.; Chaykowski, M. J. Am. Chem. Soc. 1965, 87, 1345;
8. e) Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 1135;
9. f) Smith, A. B.; Hale, K. J.; McCauley, J. P. Tetrahedron Lett. 1989, 30, 5579.
10. a) Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833;
11. b) Kocienski, P. J.; Lythgoe, B.; Waterhouse, I. J. Chem. Soc. Perkin Trans. I, 1980, 1045.
12. a) Little, R. D.; Myong, S. O. Tetrahedron Lett. 1980, 21, 3339;
13. b) Hwu, J. R. J. Org. Chem. 1983, 48 , 4432;
14. c) Baudin, J.-B.; Julia, M.; Rolando, C. Tetrahedron Lett. 1985, 26, 2333.
15. a) Smorada, R. L.; Truce, W. E. J. Org. Chem. 1979, 44, 3444;
16. b) Fabre, J-L.; Julia, M.; Verpeaux, J-N. Tetrahedron Lett. 1982, 23, 2469;
17. c) Eisch, J. J.; Berhrooz, M.; Galle, J. E. Tetrahedron Lett. 1984, 25, 4851;
18. d) Julia, M.; Righini-Tapie, A.; Verpeaux, J-N. Tetrahedron 1983, 39, 3283.
19. e) Masaki, Y.; Sakuma, K.; Kaji, K. J. Chem. Soc., Chem. Commun. 1980, 434;
20. f) Trost, B. M.; Ghadiri, M. R. J. Am. Chem. Soc. 1986, 108, 1098.
21. a) Brown, D. S.; Charreau, P.; Hansson, T.; Ley, S.V. Tetrahedron 1991, 47, 1311;
22. b) Brown, D. S.; Charreau, P.; Ley, S.V. Synlett 1990, 749;
23. c) Brown, D. S.; Bruno, M.; Davenport, R. J.; Ley, S.V. Tetrahedron 1989, 45, 4293.
24. 2 (371.47) C, 80.83; H, 6.78; N, 3.72. Found C, 80.75; H, 6.82; N, 3.67.
25. 2 furnish only complex mixtures of products in which the desired one is present in less than 10% .
26. 4 is able to promote the addition of silyl enol ethers, allyl stannanes and organometallic reagents to electrophilic substrates: a) Fry, D. F.; Fowler, C. B.; Dieter, R. K. Synlett 1994, 836; b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323; c) Henry, K. J.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett. 1992, 33, 1817; d) Reetz, M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.; Fox, D. N. A. Tetrahedron, 1992, 48, 5731; e) Arjona, O.; Perez-Ossorio, R.; Perez-Rubalcaba, A.; Quiroga, M. L. J. Chem. Soc. Chem. Commun. 1982, 452; f) Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371.
27. 4 is able to promote the addition of silyl enol ethers, allyl stannanes and organometallic reagents to electrophilic substrates: a) Fry, D. F.; Fowler, C. B.; Dieter, R. K. Synlett 1994, 836; b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323; c) Henry, K. J.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett. 1992, 33, 1817; d) Reetz, M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.; Fox, D. N. A. Tetrahedron, 1992, 48, 5731; e) Arjona, O.; Perez-Ossorio, R.; Perez-Rubalcaba, A.; Quiroga, M. L. J. Chem. Soc. Chem. Commun. 1982, 452; f) Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371.
28. 4 is able to promote the addition of silyl enol ethers, allyl stannanes and organometallic reagents to electrophilic substrates: a) Fry, D. F.; Fowler, C. B.; Dieter, R. K. Synlett 1994, 836; b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323; c) Henry, K. J.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett. 1992, 33, 1817; d) Reetz, M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.; Fox, D. N. A. Tetrahedron, 1992, 48, 5731; e) Arjona, O.; Perez-Ossorio, R.; Perez-Rubalcaba, A.; Quiroga, M. L. J. Chem. Soc. Chem. Commun. 1982, 452; f) Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371.
29. 4 is able to promote the addition of silyl enol ethers, allyl stannanes and organometallic reagents to electrophilic substrates: a) Fry, D. F.; Fowler, C. B.; Dieter, R. K. Synlett 1994, 836; b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323; c) Henry, K. J.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett. 1992, 33, 1817; d) Reetz, M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.; Fox, D. N. A. Tetrahedron, 1992, 48, 5731; e) Arjona, O.; Perez-Ossorio, R.; Perez-Rubalcaba, A.; Quiroga, M. L. J. Chem. Soc. Chem. Commun. 1982, 452; f) Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371.
30. 4 is able to promote the addition of silyl enol ethers, allyl stannanes and organometallic reagents to electrophilic substrates: a) Fry, D. F.; Fowler, C. B.; Dieter, R. K. Synlett 1994, 836; b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323; c) Henry, K. J.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett. 1992, 33, 1817; d) Reetz, M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.; Fox, D. N. A. Tetrahedron, 1992, 48, 5731; e) Arjona, O.; Perez-Ossorio, R.; Perez-Rubalcaba, A.; Quiroga, M. L. J. Chem. Soc. Chem. Commun. 1982, 452; f) Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371.
31. 4 is able to promote the addition of silyl enol ethers, allyl stannanes and organometallic reagents to electrophilic substrates: a) Fry, D. F.; Fowler, C. B.; Dieter, R. K. Synlett 1994, 836; b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323; c) Henry, K. J.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett. 1992, 33, 1817; d) Reetz, M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.; Fox, D. N. A. Tetrahedron, 1992, 48, 5731; e) Arjona, O.; Perez-Ossorio, R.; Perez-Rubalcaba, A.; Quiroga, M. L. J. Chem. Soc. Chem. Commun. 1982, 452; f) Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371.
32. 4Cl produced 2k and 2l in a ratio of 30:70. The crude mixture of regioisomers was converted into 2k by absorption on basic alumina for 24 h at room temperature.
33. Lygo, B.; O'Connor, N. Synlett 1990, 282.
34. Seebach, D.; Knochel, P. Helv. Chim. Acta 1984, 67, 261.
35. For synthetic uses of the cyano group see : Fatiadi, A. J. in The Chemistry of Triple-bonded Functional Groups; Vol. 2; Patai, S.; Rappoport, Z. Eds.; J. Wiley, Chichester, 1983; p. 1057.
36. Pal, K.; Behnke, M.L.; Tong, L. Tetrahedron Lett. 1993, 34, 6205.