Substituted benzene anions as leaving groups in the reaction of sulfinyl derivatives with Grignard reagents: A new and convenient route to dialkyl sulfoxides in high enantiomeric purity

Journal of Organic Chemistry

Volumn 65, Issue 9, 2000, Pages 2843-2846

  Capozzi, Maria Annunziata M ^a   Cardellicchio, Cosimo ^a   Naso, Francesco ^a   Tortorella, Paolo ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; BENZENE; REAGENT; SULFOXIDE; SULFUR DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0343729877     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991912q     Document Type: Article

References (34)

1. Cardellicchio, C.; Fiandanese, V.; Naso, F. J. Org. Chem. 1992, 57, 1718-1722. Cardellicchio, C.; Fiandanese, V.; Naso, F.; Scilimati, A. Tetrahedron Lett. 1992, 33, 5121-5124.
2. Cardellicchio, C.; Fiandanese, V.; Naso, F. J. Org. Chem. 1992, 57, 1718-1722. Cardellicchio, C.; Fiandanese, V.; Naso, F.; Scilimati, A. Tetrahedron Lett. 1992, 33, 5121-5124.
3. Cardellicchio, C.; Iacuone, A.; Naso, F.; Tortorella, P. Tetrahedron Lett. 1996, 37, 6017-6020.
4. Cardellicchio, C.; Fracchiolla, G.; Naso, F.; Tortorella, P. Tetrahedron 1999, 55, 525-532.
5. Capozzi, M. A. M.; Cardellicchio, C.; Fracchiolla, G.; Naso, F.; Tortorella, P. J. Am. Chem. Soc. 1999, 121, 4708-4709.
6. Durst, T.; LeBelle, M. J.; Van Der Elzen, R.; Tin, K.-C. Can. J. Chem. 1974, 52, 761-766. Lockard, J. P.; Schroeck, C. W.; Johnson, C. R. Synthesis 1973, 485-486.
7. Durst, T.; LeBelle, M. J.; Van Der Elzen, R.; Tin, K.-C. Can. J. Chem. 1974, 52, 761-766. Lockard, J. P.; Schroeck, C. W.; Johnson, C. R. Synthesis 1973, 485-486.
8. Furukawa, N.; Ogawa, S.; Matsumura, K.; Fujihara, H. J. Org. Chem. 1991, 56, 6341-6348. Ogawa, S.; Furukawa, N. J. Org. Chem. 1991, 56, 5723-5726.
9. Furukawa, N.; Ogawa, S.; Matsumura, K.; Fujihara, H. J. Org. Chem. 1991, 56, 6341-6348. Ogawa, S.; Furukawa, N. J. Org. Chem. 1991, 56, 5723-5726.
10. Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 2727-2730.
11. Satoh, T.; Kobayashi, S.; Nakanishi, S.; Horiguchi, K.; Irisa, S. Tetrahedron 1999, 55, 2515-2528 and references therein.
12. Hoffmann, R. W.; Nell, P. G. Angew. Chem., Int. Ed. Engl. 1999, 38, 338-340.
13. Evans, D. A.; Faul, M. M.; Colombo, L.; Bisaha, J. J.; Clardy, J.; Cherry, D. J. Am. Chem. Soc. 1992, 114, 5977-5985.
14. Whitesell, J. K.; Wong, M.-S. J. Org. Chem. 1994, 59, 597-601.
15. Fernandez, I.; Khiar, N.; Llera, J. M.; Alcudia, F. J. Org. Chem. 1992, 57, 6789-6796.
16. Rebiere, F.; Samuel, O.; Ricard, L.; Kagan, H. B. J. Org. Chem. 1991, 56, 5991-5999.
17. Kobayashi, K.; Yokota, K.; Akamatsu, H.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 1996, 69, 441-443. Kobayashi, K.; Kawakita, M.; Yokota, K.; Mannami, T.; Yamamoto, K.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 1995, 68, 1401-1407.
18. Kobayashi, K.; Yokota, K.; Akamatsu, H.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 1996, 69, 441-443. Kobayashi, K.; Kawakita, M.; Yokota, K.; Mannami, T.; Yamamoto, K.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 1995, 68, 1401-1407.
19. (a) Brunel, J. M.; Kagan, H. B. Synlett 1996, 404-406.
20. (b) Zhao, S. H.; Samuel, O.; Kagan, H. B. Tetrahedron 1987, 43, 5135-5144.
21. (c) Pitchen, P.; Duñach, E.; Deshmukh, M. N.; Kagan, H. B. J. Am. Chem. Soc. 1984, 106, 8188-8193.
22. Bortolini, O.; Di Furia, F.; Licini, G.; Modena, G.; Rossi, M. Tetrahedron Lett. 1986, 27, 6257-6260. Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325-327.
23. Bortolini, O.; Di Furia, F.; Licini, G.; Modena, G.; Rossi, M. Tetrahedron Lett. 1986, 27, 6257-6260. Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325-327.
24. Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S.J. Org. Chem. 1993, 58, 7624-7626. Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 4529-4533.
25. Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S.J. Org. Chem. 1993, 58, 7624-7626. Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 4529-4533.
26. Bolm, C.; Müller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305-315.
27. Racemic 3: Bordwell, F. G.; Boutan, P. J. J. Am. Chem. Soc. 1957, 79, 717-722.
28. Brunel, J.-M.; Diter, P.; Duetsch, M.; Kagan, H. B. J. Org. Chem. 1995, 60, 8086-8088.
29. Imboden, C.; Renaud, P. Tetrahedron: Asymmetry 1999, 10, 1051-1060.
30. Burgess, K.; Henderson, I. Tetrahedron 1991, 47, 6601-6616.
31. Racemic 7: Banerji, K. K. J. Chem. Soc., Perkin Trans. 2 1991, 759-763.
32. Racemic 11: Entwistle, I. D.; Johnstone, R. A. W. Chem. Commun. 1965, 29-30.
33. Racemic 12: Chada, V. K.; Leidal, K. G.; Plapp, B. V. J. Med. Chem. 1983, 26, 916-922.
34. Racemic 13: Jerchel, D.; Dippelhofer, L.; Renner, D. Chem. Ber. 1954, 87, 947-955.