Synthesis of enantiomerically pure β-azidoselenides starting from natural terpenes

Tetrahedron

Volumn 63, Issue 50, 2007, Pages 12373-12378

  Tiecco, Marcello ^a   Testaferri, Lorenzo ^a   Santi, Claudio ^a   Tomassini, Cristina ^a   Santoro, Stefano ^a   Marini, Francesca ^a   Bagnoli, Luana ^a   Temperini, Andrea ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

( 2 AZIDO 5 ISOPROPYL 2 METHYLCYCLOHEXYL)(PHENYL)SELANE; ( 4 AZIDO 4,7,7 TRIMETHYLBICYCLO[4.1.0] HEPTAN 3 YL)(PHENYL)SELANE; (( 4 AZIDO 1,1,7 TRIMETHYLDECAHYDRO 1H CYCLOPROPA[E]AZULEN 4 YL)METHYL)(PHENYL)SELANE; (2 AZIDO 2 ( 4 AZIDO 4 METHYL 3 (PHENYLSELENENYL)CYCLOHEXYL)PROPYL)(PHENYL)SELANE; 3,7,7 TRIMETHYL 4 (PHENYLSELENENYL)BICYCLO[4.1.0]HEPTAN 3 AMINE; 4,7 DIMETHYL 7 (PHENYLSELENENYLMETHYL) 6 OXABICYCLO[3.2.1]OCT 3 ENE; 5 (2 AZIDO 1 (PHENYLSELENENYL)PROPAN 2 YL) 2 METHYLCYCLOHEX 2 ENONE; 7 AZIDO 3,7 DIMETHYL 6 (PHENYLSELENENYL)OCTANAL; BETA AZIDOSELENIDE DERIVATIVE; N ( 3,7,7 TRIMETHYL 4 (PHENYLSELENENYL)BICYCLO[4.1.0]HEPTAN 3 YL)ACETAMIDE; N ( 3,7,7 TRIMETHYL 4 (PHENYLSELENENYL)BICYCLO[4.1.0]HEPTAN 3 YL)BENZAMIDE; SELENIDE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 35549008797     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.047     Document Type: Article

References (27)

1. Sheradsky T. In: Patai S. (Ed). The Chemistry of the Azido Group (1971), Wiley-Interscience, New York, NY
2. Scriven E.F.V., and Turbull K. Chem. Rev. 88 (1988) 297-368
3. Bräse S., Gil C., Knepper K., and Zimmermann V. Angew. Chem., Int. Ed. 44 (2005) 5188-5240
4. Tiecco M., Testaferri L., Temperini A., Bagnoli L., Marini F., and Santi C. Synth. Commun. 28 (1998) 2167-2179
5. Riela S., Aprile C., Gruttadauria M., Lo Melo P., and Noto R. Molecules 10 (2005) 383-393
6. Ward V.R., Cooper N.A., and Ward A.P. J. Chem. Soc., Perkin Trans. 1 (2001) 944-945
7. Broggini G., Molteni G., and Zucchi G. Synthesis (1995) 647-648
8. Denis J.N., Vicens J., and Krief A. Tetrahedron Lett. 20 (1979) 2697-2700
9. Hasser A., and Amarasekara A.S. Tetrahedron Lett. 28 (1987) 5185-5188
10. Giuliano R.M., and Duarte F. Synlett (1992) 419-421
11. Tingoli M., Tiecco M., Chianelli D., Balducci R., and Temperini A. J. Org. Chem. 56 (1991) 6809-6813
12. He L., Byun H.S., and Bittman R. J. Org. Chem. 65 (2000) 7627-7633
13. Alvarez de Cienfuegos L., Rodriguez C., Mota A.J., and Robles R. Org. Lett. 5 (2003) 2743-2745
14. Enders D., and Klein D. Synlett (1999) 719-720
15. Martinez L.E., Leighton J.L., Carsten D.H., and Jacobsen E.N. J. Am. Chem. Soc. 117 (1995) 5897-5898
16. Hodgson D.M., Gibbs A.R., and Lee G.P. Tetrahedron 52 (1996) 14361-14384
17. Rondon A.C., and Panek J.S. Chemtracts 10 (1997) 1058-1061
18. Gianneschi N.C., Bertin P.A., Nguyen S.T., Mirkin C.A., Zakharov L.N., and Rheingold A.L. J. Am. Chem. Soc. 125 (2003) 10508-10509
19. Tiecco M., Testaferri L., Santi C., Tomassini C., Marini F., Bagnoli L., and Temperini A. Angew. Chem., Int. Ed. 42 (2003) 3131-3133
20. Tiecco M., Testaferri L., Bagnoli L., Marini F., Temperini A., Tomassini C., and Santi C. Tetrahedron Lett. 41 (2000) 3241-3245
21. Tiecco M., Testaferri L., Santi C., Tomassini C., Marini F., Bagnoli L., and Temperini A. Chem.-Eur. J. 8 (2002) 1118-1124
22. Tiecco M., Testaferri L., Marini F., Sternativo S., Temperini A., Bagnoli L., and Santi C. Tetrahedron: Asymmetry 12 (2001) 1493-1502
23. Tiecco M., Testaferri L., Bagnoli L., Purgatorio V., Temperini A., Marini F., and Santi C. Tetrahedron: Asymmetry 12 (2001) 3297-3304
24. For recent reviews on these asymmetric selenenylation reactions, see:. Browne D.M.M., and Wirth T. Curr. Org. Chem. 10 (2006) 1893-1903 and
25. Tiecco M., Testaferri L., Bagnoli L., Marini F., Santi C., Temperini A., Scarponi C., Sternativo S., Terlizzi R., and Tomassini C. Arkivoc (2006) 186-206
26. Furst A., and Plattner P.A. Helv. Chim. Acta 32 (1949) 275-281
27. Gemal A.L., and Luche J.L. J. Am. Chem. Soc. 103 (1981) 5454-5459