A facile stereospecific synthesis of chiral β-keto sulfoxides

Tetrahedron Asymmetry

Volumn 10, Issue 18, 1999, Pages 3463-3466

  Caputo, Romualdo ^a   Giordano, Federico ^a   Guaragna, Annalisa ^a   Palumbo, Giovanni ^a   Pedatella, Silvana ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; OXIDATION; PRIORITY JOURNAL; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033461155     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00350-X     Document Type: Article

References (12)

1. Solladié, G.; Carreño, M. C. In Organosulfur Chemistry. Synthetic Aspects: Optically Active β-Keto Sulfoxides and Analogues in Asymmetric Synthesis; Page, P., Ed.; Academic Press: London, 1995; pp. 1-47.
2. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1345-1353.
3. Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
4. Schneider, F.; Simon, R. Synthesis 1986, 582-584.
5. Carreño, M. C.; García Ruano, J. L.; Pedregal, C.; Rubio, A. J. Chem. Soc., Perkin Trans. 1 1989, 1335-1337.
6. Caputo, R.; Longobardo, L.; Palumbo, G.; Pedatella, S. Synlett 1995, 1274.
7. Aggarwal, V. K.; Evans, G.; Moya, E.; Dowden, J. J. Org. Chem. 1992, 57, 6390-6391.
8. Di Furia, F.; Licini, G.; Modena, G. Gazz. Chim. Ital. 1990, 120, 165-170.
9. α radiation.
10. (Formula Presented) Least squares refinement of 1154 reflections with I>3σ(I) converged upon the structure with R=0.033, Rw=0.041 and a goodness of fit=1.172. The inverted structure converged with the following values: R=0.037, Rw=0.046. Correspondence regarding the X-ray data should be addressed to F.G.
11. Pirkle, W. H.; Beare, S. D.; Muntz, R. L. Tetrahedron Lett. 1974, 2295-2298.
12. Solladié, G.; Demailly, G.; Greck, C. Tetrahedron Lett. 1985, 26, 435-438.