Tin(IV) triflimidate-catalyzed cyclization of epoxy esters to functionalized δ-hydroxy-γ-lactones

Tetrahedron Letters

Volumn 50, Issue 21, 2009, Pages 2536-2539

  Antoniotti, Sylvain ^a   Duñach, Elisabet ^a  

^a UNIVERSITÉ CÔTE D'AZUR   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DELTA HYDROXY GAMMA LACTONE DERIVATIVE; EPOXYPROPARGYL ESTER; ESTER DERIVATIVE; LACTONE DERIVATIVE; TIN; TIN (IV) TRIFLIMIDATE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLIZATION;

EID: 63749132620     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.055     Document Type: Article

References (43)

1. Trost B.M. Angew. Chem., Int. Ed. Engl. 34 (1995) 259-281
2. Grubbs R.H. Tetrahedron 60 (2004) 7117-7140
3. In: Beller M., and Bolm C. (Eds). Transition Metals for Organic Synthesis. 2nd ed. (2004), Wiley-VCH, Verlag GmbH & Co. KGaA, Weinheim
4. Michelet V., Toullec P.Y., and Genêt J.-P. Angew. Chem., Int. Ed. 47 (2008) 4268-4315
5. Aubert C., Buisine O., and Malacria M. Chem. Rev. 102 (2002) 813-834
6. Jimenez-Nunez E., and Echavarren A.M. Chem. Commun. (2007) 333-346
7. Hashmi A.S.K. Chem. Rev. 107 (2007) 3180-3211
8. Zhang L., Sun J., and Kozmin S.A. Adv. Synth. Catal. 348 (2006) 2271-2296
9. Yamamoto Y. J. Org. Chem. 72 (2007) 7817-7831
10. Ma S. Pure Appl. Chem. 78 (2006) 197-208
11. Yamamoto H., and Futatsugi K. Angew. Chem., Int. Ed. 44 (2005) 1924-1942
12. Oe Y., Ohta T., and Ito Y. Synlett (2005) 179-181
13. Shen H.C. Tetrahedron 64 (2008) 3885-3903
14. Tietze L.F., and Kinzel T. Pure Appl. Chem. 79 (2007) 629-650
15. Chapman C.J., and Frost C.G. Synthesis (2007) 1-21
16. Tietze L.F. Chem. Rev. 96 (1996) 115-136
17. Padwa A., and Bur S.K. Tetrahedron 63 (2007) 5341-5378
18. Coulombel L., Favier I., and Duñach E. Chem. Commun. (2005) 2286-2288
19. Coulombel L., Rajzmann M., Pons J.-M., Olivero S., and Duñach E. Chem. Eur. J. 12 (2006) 6356-6365
20. Chaminade X., Coulombel L., Olivero S., and Duñach E. Eur. J. Org. Chem. (2006) 3554-3557
21. Weiwer M., Coulombel L., and Duñach E. Chem. Commun. (2006) 332-334
22. Chaminade X., Chiba S., Narasaka K., and Dunach E. Tetrahedron Lett. 49 (2008) 2384-2387
23. Grau F., Heumann A., and Duñach E. Angew. Chem., Int. Ed. 45 (2006) 7285-7289
24. Tsuji H., Yamagata K.-I., Itoh Y., Endo K., Nakamura M., and Nakamura E. Angew. Chem., Int. Ed. 46 (2007) 8060-8062
25. Dai L.-Z., Qi M.-J., Shi Y.-L., Liu X.-G., and Shi M. Org. Lett. 9 (2007) 3191-3194
26. Dai L.-Z., and Shi M. Chem. Eur. J. 14 (2008) 7011-7018
27. Hashmi S.A.K., and Sinha P. Adv. Synth. Catal. 346 (2004) 432-438
28. Ji K.-G., Shen Y.-W., Shu X.-Z., Xiao H.-Q., Bian Y.-J., and Liang Y.-M. Adv. Synth. Catal. 350 (2008) 1275-1280
29. Shu X.-Z., Liu X.-Y., Xiao H.-Q., Ji K.-G., Guo L.-N., Qi C.-Z., and Liang Y.M. Adv. Synth. Catal. 349 (2007) 2493-2498
30. Hashmi A., Stephen K., Bührle M., Salathé R., and Bats J.W. Adv. Synth. Catal. 350 (2008) 2059-2064
31. Shu X.-Z., Liu X.-Y., Ji K.-G., Xiao H.-Q., and Liang Y.-M. Chem. Eur. J. 14 (2008) 5282-5289
32. Cordonnier M.-C., Blanc A., and Pale P. Org. Lett. 10 (2008) 1569-1572
33. Antoniotti S., and Duñach E. Chem. Commun. (2008) 993-995
34. Nacro K., Baltas M., Escudier J.-M., and Gorrichon L. Tetrahedron 53 (1997) 659-672
35. Justicia J., Oller-Lopez J.L., Campana A.G., Oltra J.E., Cuerva J.M., Bunuel E., and Cardenas D.J. J. Am. Chem. Soc. 127 (2005) 14911-14921
36. Bernard A.M., Frongia A., Piras P.P., and Secci F. Org. Lett. 5 (2003) 2923-2926
37. Ferrié L., Reymond S., Capdevielle P., and Cossy J. Synlett (2007) 2891-2893
38. Quinn K.J., Isaacs A.K., and Arvary R.A. Org. Lett. 6 (2004) 4143-4145
39. Trost B.M., and Rhee Y.H. J. Am. Chem. Soc. 121 (1999) 11680-11683
40. Beesley R.M., Ingold C.K., and Thorpe J.F. J. Chem. Soc., Perkin Trans. 107 (1915) 1080-1106
41. We previously observed a similar stereoselectivity in the cyclization of 1,6-dienes with substrates bearing only one ester group: see Ref. 23.
42. Muñoz M.P., and Lloyd-Jones G.C. Eur. J. Org. Chem. 2009 (2009) 516-524
43. 5Na, 277.10464; found 277.10446.