A new and general synthesis of chiral β-ketosulfoxides by reaction of (+)-(R)-methyl p-tolyl sulfoxide with nitriles

Tetrahedron Letters

Volumn 40, Issue 52, 1999, Pages 9301-9303

  Vleggaar, Robert ^a   Zeevaart, Jacob G ^a  

^a UNIVERSITY OF PRETORIA   (South Africa)

Author keywords

Carbon carbon bond formation; Chiral ketosulfoxides; Chiral sulfoxides; Nitriles

Indexed keywords

NITRILE; SULFOXIDE;

ARTICLE; CHEMICAL BINDING; CHEMICAL MODIFICATION; CHIRALITY; REACTION ANALYSIS; SYNTHESIS;

EID: 0033601446     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01951-6     Document Type: Article

References (17)

1. Allin, S. M.; Shuttleworth, S. J.; Page, P. C. B. In Organosulfur Chemistry. Vol. 2: Synthetic and Stereochemical Aspects; Page, P., Ed.; Academic Press: London, 1998; pp. 97-155.
2. Carreño, M. C. Chem. Rev. 1995, 95, 1717.
3. (a) Kunieda, N.; Nokami, J.; Kinoshita, M. Chem. Lett. 1974, 369.
4. (b) Solladié, G.; Carreño, M. C. In Organosulfur Chemistry, Vol. 1: Synthetic Aspects; Page, P., Ed.; Academic Press: London, 1995; pp. 1-47.
5. Solladié, G. Synthesis 1981, 185.
6. Zeevaart, J. G. M.Sc. Thesis, University of Pretoria, 1997.
7. (a) Bezuidenhout, S. C.; Gelderblom, W. C. A.; Gorst-Allman, C. P.; Horak, R. M.; Marasas, W. F. O.; Spiteller, G.; Vleggaar, R. J. Chem. Soc., Chem. Commun. 1988, 743.
8. (b) Boer, A. M.Sc. Thesis, University of Pretoria, 1992.
9. Solladié, G.; Greck, C.; Demailly, G.; Solladié-Cavallo, A. Tetrahedron Lett. 1982, 23, 5047.
10. Solladié, G.; Huser, N. Rec. Trav. Chim. Pays-Bas 1995, 114, 153.
11. 3) in agreement with published values.
12. 13C NMR, and HR FAB-MS data were obtained for all compounds.
13. 2O, 92%.
14. Schneider, F.; Simon, R. Synthesis 1986, 582.
15. Annunziata, R.; Cinquini, M.; Cozzi, F. J. Chem. Soc., Perkin Trans. 1 1979, 1687.
16. Banfi, L.; Colombo, L.; Gennari, C.; Annunziata, R.; Cozzi, F. Synthesis 1982, 829.
17. Kunieda, N.; Motoki, H.; Kinishita, N. Chem. Lett. 1978, 713.