(S)-(+)-3-p-tolylsulfinylbut-3-en-2-one : A spectacular oxabutadiene for asymmetric cycloaddition of styrenic compounds

Tetrahedron Letters

Volumn 37, Issue 21, 1996, Pages 3687-3690

  Hayes, Patricia ^a   Dujardin, Gilles ^a   Maignan, Christian ^a  

^a UNIVERSITÉ DU MAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

STYRENE DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029945911     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00619-3     Document Type: Article

References (12)

1. (a) Carreño, M.C. Chem. Rev., 1995, 95, 1717-1760 ;
2. (b) Drabowicz, J. ; Kielbasinski, P. ; Mikolajezyk, M. Synthesis of sulfoxides in "The Chemistry of Sulfones and Sulfoxides" Patai, S.; Rappoport, Z. and Stirling, C. Eds., John Wiley & Sons Inc.; Colchester, Essex, Great Britain (1988), Chapter 8.
3. Gosselin, P. ; Bonfand, E. ; Hayes, P. ; Retoux, R. ; Maignan, C. Tetrahedron Asymmetry 1994, 5, 781-784.
4. 13C-RMN δ 12.5/13.8, 17.4/17.6, 21.3/21.4, 33.7/34.4, 50.1/50.4, 55.3, 100.8/101.5, 113.7/113.8, 115.1/115.2, 124.3/124.4, 127.3, 129.6, 131.7/132.0, 139.5, 140.2, 155.5/155.8, 159.6.
5. The determination of absolute configuration of adducts 5 is under progress by X-Ray crystallography and by chemical correlation to known enantiopure lactones and will be published in a full paper.
6. 3 for example) has been unsuccessfully carried out in the case of ethyl vinyl ether.
7. -1. (formula presented)
8. Smith, CW.; Norton, D.; Ballard, S. J. Am. Chem. Soc., 1951, 73, 5273-5280.
9. Ismail, ZM.; Hoffmann, H.M.R. Angew. Chem. Int. Ed. Engl., 1982, 21, 859-860.
10. Hall, Jr. H.K.; Abdelkader, M. J. Org. Chem., 1981, 46, 2948-2853.
11. Schmidt, R.R.; Frich, W.; Haag-Zeino, B.; Apparao, S. Tetrahedron Lett., 1987, 28, 4045-4048.
12. Dujardin, G.; Maudet, M.; Brown, E. Tetrahedron Lett., 1994, 46, 8619-8622.