Michael Additions of α-Sulfinyl and α-Sulfonyl Carbanions: The Unprecedented Reaction of β-Keto Sulfoxides and β-Keto Sulfones with Highly Stabilized Michael Acceptors

Journal of Organic Chemistry

Volumn 60, Issue 21, 1995, Pages 6678-6679

  Marco, José Luis ^a,b,c,d   Fernández, Inmaculada ^a,b,c   Khiar, Noureddine ^a,b,c,d   Fernández, Paloma ^a,b,c   Romero, Antonio ^a,b,c  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b UNIVERSITY OF SEVILLE   (Spain)

^c INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^d CSIC C/Juan Cierva 3 28006 M   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001647787     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00126a014     Document Type: Article

References (18)

1. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Tetrahedron Organic Chemistry Series No. 9; Pergamon Press: Oxford, 1992.
2. Simpkins, N. S. Sulfones in Organic Synthesis; Tetrahedron Organic Chemistry Series No. 10; Pergamon Press: Oxford, 1993.
3. Posner, G. H. In The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; New York, 1988; pp 823.
4. Solladie, G. Synthesis 1981, 185.
5. Boger, D. L.; Mullican, M. D. J. Org. Chem. 1980, 45, 5002.
6. Nozaki, H.; Mori, T.; Kawanisi, M. Can. J. Chem. 1968, 46, 3767.
7. Russell, G. A.; Ochrymowycz, L. A. J. Org. Chem. 1969, 34, 3624.
8. Vig, O. P.; Matta, K. L.; Sehgal, J. M.; Sharma, S. D. J. Indian Chem. Soc. 1970, 47, 894.
9. Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123.
10. Khiar, N.; Fernandez, I.; Alcudia, F.; Hua, D. H. Tetrahedron Lett. 1993, 34, 699.
11. To our knowledge, only the Michael addition of (phenylsulfinyl)-acetone to dimethyl ethylideneacetoacetate or benzylideneacetoacetate has been reported and described as having poor results: Jaxa-Chamiec, A. A.; Sammes, P. G.; Kennewell, P. D. J. Chem. Soc, Perkin Trans. 1 1980, 170.
12. Kuthan, J. Adv. Heterocycl. Chem. 1983, 34, 146.
13. Kazmer, J. S.; Daddona, P. E.; Dalke, A. P.; Kelley, W. N. Biochem. Pharmacol. 1983, 32, 805.
14. Alcudia, F.; Fernandez, I.; Trujillo, M.; Zorrilla, F. Tetrahedron 1989, 45, 1491 and references cited therein. When not specifically stated, the β-sulfoxides used and the 2-amino-4ff-pyrans obtained here are racemic samples.
15. Soto, J. L.; Seoane, C.; Martin, N.; Blanco, L. A. Heterocycles 1983, 20, 803.
16. Garcia-Ruano, J. L.; Pedregal, C.; Rodríguez, J. H. Tetrahedron 1987, 43, 4407
17. Davis, R.; Kern, J. R.; Kurz, L. J.; Pfister, J. R. J. Am. Chem. Soc. 1988, 110, 7873 and references cited therein.
18. Jones, G. B.; Chapman, B. J. Synthesis 1995, 475.