Synthesis of enantiomerically pure mono-, di- and trisubstituted 2-sulfinylbuta-1,3-dienes, via β-hydroxy selenides

Synthesis

Volumn , Issue 9, 1996, Pages 1079-1081

  Gosselin, Pascal ^a   Bonfand, Eric ^a   Maignan, Christian ^a  

^a UNIVERSITÉ DU MAINE   (France)

Author keywords

(+) (R) p tolyl vinyl sulfoxide; 2 sulfinyldienes; Krief Reich elimination; hydroxy selenides

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ORGANOSULFUR DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029812349     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4348     Document Type: Article

References (12)

1. Bonfand, E.; Gosselin, P.; Maignan, C. Tetrahedron: Asymmetry 1993, 4, 1167.
2. Gosselin, P.; Bonfand, E.; Hayes, P.; Retoux, R.; Maignan, C. Tetrahedron: Asymmetry 1994, 5, 781.
3. Bonfand, E.; Gosselin, P.; Maignan, C. Electronic Conference on Trends in Organic Chemistry (ECTOC 1), 1995, http:// www.ch.ic.ac.uk/ectoc/papers/
4. b have not been applied to the preparation of trisubstituted 2-sulfinylbuta-1,3-dienes: (a) Paley, R. S.; Weers, H. L.; Fernandez, P. Tetrahedron Lett. 1995, 36, 3605. (b) Aversa, M. C.; Bonaccorsi, P.; Giannetto, P.; Jafari, S. M. A.; Neville Jones, D.; Tetrahedron : Asymmetry 1992, 3, 701.
5. b have not been applied to the preparation of trisubstituted 2-sulfinylbuta-1,3-dienes: (a) Paley, R. S.; Weers, H. L.; Fernandez, P. Tetrahedron Lett. 1995, 36, 3605. (b) Aversa, M. C.; Bonaccorsi, P.; Giannetto, P.; Jafari, S. M. A.; Neville Jones, D.; Tetrahedron : Asymmetry 1992, 3, 701.
6. Ronan, B.; Kagan, H. B. Tetrahedron : Asymmetry 1992, 3, 115-122.
7. Suzuki, H., Fuchita, T.; Iwasa, A. Synthesis 1978, 905.
8. 2H, NaI/TFAA or NaI/TMSCl, led to the unexpected 3-para-tolylsulfanylbutan-2-one, as the major or single product.
9. Lerouge, P.; Paulmier, C. Bull. Soc. Chim. Fr. 1985, 1219.
10. Ryu, I.; Muraï, S.; Niwa, I.; Sonoda, N. Synthesis 1977, 874.
11. Rémion, J.; Krief, A. Tetrahedron Lett. 1976, 41, 3743.
12. Reich, H. J.; Chow, F.; Shah, S.K. J. Am. Chem. Soc. 1979. 101, 6638.