Grubbs catalyst promoted oxacycloisomerization: An easy route to bicyclic dihydrofurans and tricyclic acetals

Synlett

Volumn , Issue 10, 2009, Pages 1597-1600

  Taleb, Assya ^a,b   Lahrech, Mokhtar ^b   Hacini, Salih ^b   Thibonnet, Jérôme ^c   Parrain, Jean Luc ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

^b UNIVERSITY OF ORAN   (Algeria)

^c UNIVERSITÉ DE TOURS   (France)

Author keywords

1 hydroxy 2 propargyl cyclic derivatives; Bicyclic dihydrofuran; Grubbs I catalyst; Oxacycloisomerization; Tricyclic acetals

Indexed keywords

ACETAL DERIVATIVE; ALKYNE DERIVATIVE; FURAN DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERIZATION; RING CLOSING METATHESIS; SYNTHESIS;

EID: 67649407421     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217341     Document Type: Article

References (25)

1. (a) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 217.
2. (b) Merritt, A. T.; Ley, S. V. Nat. Prod. Rep. 1992, 9, 243.
3. (c) Schoop, A.; Greiving, H.; Gohrt, A. Tetrahedron Lett. 2000, 41, 1913.
4. (d) Schabbert, S.; Schaumann, E. Eur. J. Org. Chem. 1998, 1873.
5. (e) Mortensen, D. S.; Rodriguez, A. L.; Carlson, K. E.; Sun, J.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. J. Med. Chem. 2001, 44, 3838.
6. (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
7. (b) Garzino, F.; Meou, A.; Brun, P. Eur. J. Org. Chem. 2003, 1410.
8. Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 2002, 124, 2528.
9. Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 2003, 125, 7482.
10. Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 26, 4161.
11. Koo, B.; McDonald, F. E. Org. Lett. 2005, 7, 3621.
12. (a) Wang, Z.; Lu, X. J. Org. Chem. 1996, 61, 2254.
13. (b) Murakami, H.; Matsui, Y.; Ozawa, F.; Yoshifuji, M. J. Organomet. Chem. 2006, 691, 3151.
14. (a) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654.
15. (b) Antoniotti, S.; Genin, E.; Michelet, V.; Genêt, J. P. J. Am. Chem. Soc. 2005, 127, 9976.
16. Matovic, R.; Ivkovic, A.; Manojlovic, M.; Tokic-Vujosevic, Z.; Saicic, R. N. J. Org. Chem. 2006, 71, 9411.
17. Barco, A.; Benetti, S.; Pollini, G. P. Synthesis 1973, 316.
18. Barbier, P. C. R. Hebd. Seances Acad. Sci. 1898, 128.
19. Lai, Y. H. Synthesis 1981, 585.
20. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
21. Ruthenium(II) complexes are known to promote addition of oxygen nucleophiles to alkynes, see: (a) Mitsudo, T.; Hori, Y.; Yamakawa, Y.; Watanabe, Y. J. Org. Chem. 1987, 52, 2230.
22. (b) Neveux, M. I.; Seiller, B.; Hagedorn, F.; Bruneau, C.; Dixneuf, P. H. J. Organomet. Chem. 1993, 451, 133.
23. 2O).
24. +], 133(38), 134(35), 135(35), 136(12), 144(16), 145(36), 147(44), 148(14), 151(11), 161(27), 162(81), 163(100), 164(16), 91(90), 92(22), 93(32), 94(13), 95(30), 97(14), 104(11), 105(38), 106(22), 107(36), 108(11), 111(17), 117(20), 119(39), 120(34), 121(34), 123(17), 50(13), 51(18), 53(19), 55(82), 65(40), 67(42), 69(13), 70(16), 77(55), 78(13), 79(63), 81(14), 83(21).
25. For examples of implications of metal vinylidene in catalysis, see: Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311.