Synthesis and Diels-Alder reactions of enantiopure (-)-trans-benzo[d]-dithüne-S,S′-dioxide

Tetrahedron Asymmetry

Volumn 7, Issue 2, 1996, Pages 369-372

  Cecchet, Elisa ^a   Di Furia, Fulvio ^a   Licini, Giulia ^a   Modena, Giorgio ^a  

^a UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DITHIANE DERIVATIVE; SULFOXIDE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030058063     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00008-0     Document Type: Article

References (16)

1. "The Chemistry of Sulphones and Sulphoxides" Patai, S.; Rappoport, Z. and Stirling, C. Eds., John Wiley & Sons Inc., Colchester, Essex, Great Britain (1988); De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755;
2. "The Chemistry of Sulphones and Sulphoxides" Patai, S.; Rappoport, Z. and Stirling, C. Eds., John Wiley & Sons Inc., Colchester, Essex, Great Britain (1988); De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755;
3. Arai, Y; Koizumi, T Sulfur Reports 1993, 15, 41.
4. Benzo[d]dithiine 1 was obtained via reaction of the disodium salt of the benzene-1,2-dithiol (Fluka) with cis-1,2-dichloroethylene in ca. 70% yield.
5. Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325.
6. 1H NMR in the presence of (S)-(+) or (R)-(-)-1-(9-anthryl)-2,2,2-trifluoroethanol.
7. 25= -257 (C=1.1, chloroform)].
8. 25=+50 (c=0.1, chloroform).
9. 1H NMR.
10. Bertotti, E.; Luciani, G.; Montanari, F. Gazzetta Chim. It. 1959, 89, 1564; Cinquini, M.; Colonna, S.; Montanari, F. J. Chem. Soc. C, 1970, 572.
11. Bertotti, E.; Luciani, G.; Montanari, F. Gazzetta Chim. It. 1959, 89, 1564; Cinquini, M.; Colonna, S.; Montanari, F. J. Chem. Soc. C, 1970, 572.
12. Valle, G. unpublished.
13. Cossu, S.; De Lucchi, O.; Fabbri, D.; Licini, G.; Pasquato, L. Org. Prep. Proced. Int. 1991, 23, 573.
14. Aggarwal V., Drabowicz J., Grainger R.S., Gultekin Z., Lightowler M., Spargo, P.L. J. Org. Chem. 1995, 60, 4962.
15. The reduced and variable diastereoselection obtained with furan may be due to the reversibility of the cycloaddition reaction.
16. 1H NMR spectra of cycloadduct (+)-7c are modified by changing the temperature (20-65°C), thus indicating the presence of an equilibrium between conformers. Unfortunately, some of the signals are still broad at high temperature.