Investigating thio-analogues of PSE acetals: A more complex reaction

Tetrahedron Letters

Volumn 44, Issue 30, 2003, Pages 5723-5725

  Cabianca, Elena ^a,b   Tatibouët, Arnaud ^a   Chéry, Florence ^a   Pillard, Christelle ^a   De Lucchi, Ottorino ^b   Rollin, Patrick ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; HYDROXYLATION; RING CLOSING METATHESIS;

EID: 0038166608     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01303-0     Document Type: Article

References (22)

1. Chéry F., Rollin P., De Lucchi O., Cossu S. Synthesis. 2001;286-292.
2. Cabianca E., Chéry F., Rollin P., Tatibouët A., De Lucchi O. Tetrahedron Lett. 43:2002;585-587.
3. Eliel E.L., Morris-Natschke S.J. J. Am. Chem. Soc. 106:1984;2937-2942.
4. Utimoto K., Nakamura A., Matsubara S. J. Am. Chem. Soc. 112:1990;8189-8190.
5. Cossu S., De Lucchi O., Fabris F., Ballini R., Bosica G. Synthesis. 1996;1481-1484.
6. +=245.0.
7. +=267.0.
8. De Voss J.J., Sui Z. Tetrahedron Lett. 35:1994;49-52.
9. Ioannou M., Porter M.J., Saez F. Chem. Commun. 2002;346-347.
10. Bulman-Page P.C., Ley S.V., Morton J.A., Williams D.J. J. Chem. Soc., Perkin Trans. 1. 1981;457-461.
11. +=409.0.
12. +=267.0.
13. +=345.0.
14. BPSE is commercially available in both Z- and E-stereoforms.
15. Retention of configuration in Michael additions on BPSE was initially reported by Meek and Fowler. See: Meek J.S., Fowler J.S. J. Org. Chem. 33:1968;985-991.
16. +=267.0.
17. +=281.0.
18. (E)-BPSE analogously afforded a 54% yield of 15E .
19. +=329.0.
20. +=329.0.
21. +=329.0.
22. De Lucchi O., Lucchini V., Marchioro C., Modena G. Tetrahedron Lett. 26:1985;4539-4542.