A simple and efficient enantioselective synthesis of 2-alkylidene-3-alkyl-1,4-benzodioxanes by palladium-catalyzed annulation of benzene-1,2-diol and propargylic carbonates

Organic Letters

Volumn 2, Issue 4, 2000, Pages 527-529

  Labrosse, Jean Robert ^a   Lhoste, Paul ^a   Sinou, Denis ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000746219     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9913791     Document Type: Article

References (23)

1. (a) Nelson, W. L.; Wennerstrom, J. E.; Dyer, D. C.; Engel, M. J. Med. Chem. 1977, 20, 880.
2. (b) Marciniak, G.; Delgado, A.; Leclerc, G.; Velly, J.; Decker, N.; Schwartz, J. J. Med. Chem. 1989, 32, 1402.
3. (c) Ruffolo, R. R., Jr.; Boudinell, W.; Hieble, J. P. J. Med. Chem. 1995, 38, 3681.
4. (d) Giardina, D.; Bertini, R.; Brancia, E.; Brasili, L.; Melchiore, C. J. Med. Chem. 1985, 28, 1354.
5. (e) Quaglia, W.; Pigini, M.; tayebati, S. K.; Piergentili, A.; Giannella, M.; Leonardi, A.; Taddei, C.; Melchiorre, C. J. Med. Chem. 1996, 39, 2253.
6. Satoh, Y.; Powers, C.; Toledo, L. M.; Kowalski, T. J.; Peters, P. A.; Kimble, E. F. J. Med. Chem. 1995, 38, 68.
7. (a) Fagan, G. P.; Chapleo, C. P.; Lane, A. C.; Myers, M.; Roach, A. G.; Roach, C. F. C.; Stillings, M. R.; Welbourn, A. P. J. Med. Chem. 1988, 31, 944.
8. (a) Cabiddu, S.; Floria, C.; Melis, S.; Sotgiu, F.; Cerioni, G. J. Heterocycl. Chem. 1986, 23, 1815.
9. (b) Rosnati, V.; Salimbeni, A. Tetrahedron 1986, 42, 4541.
10. (c) Ruiz, N.; Rollin, P. Tetrahedron Lett. 1989, 30, 1637.
11. (d) Moreau, P.; Neirabeyeh, M. Al.; Guillaumet, G.; Coudert, G. Tetrahedron Lett. 1991, 32, 5525.
12. (e) Chowdhury, C.; Kundu, N. G. Chem. Commun. 1996, 1067.
13. (f) Chowdhury, C.; Chaudhury, G.; Guha, S.; Mukherjee, A. K.; Kundu, N. G. J. Org. Chem. 1998, 63, 1863.
14. (g) Basak, A.; Bhattacharya, G.; Mallik, U. K.; Khamrai, U. K. Synth. Commun. 1997, 27, 367.
15. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
16. (a) Yamamoto, K.; Tsuji, J. Tetrahedron Lett. 1982, 23, 3089.
17. (b) Genet, J. P.; Grisoni, S. Tetrahedron Lett. 1989, 29, 4543.
18. (c) Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3531.
19. (d) Zenner, J. M.; Larock, R. C. J. Org. Chem. 1999, 64, 7312.
20. Labrosse, J. R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1999, 40, 9025.
21. (a) Larock, R. C.; Berrios-Peña, N. G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615.
22. (b) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482.
23. (c) Larock, R. C.; He, Y.; Leong, W. W.; Han, X.; Refvik, M. D.; Zenner, J. M. J. Org. Chem. 1998, 63, 2154.