Homopropargylic Alcohols from Propargylic Derivatives via Butyltelluro Allene Compounds

Synlett

Volumn 1996, Issue 6, 1996, Pages 526-528

  Dabdoub, Miguel J ^a   Rotta, Jeane C G ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005238180     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5494     Document Type: Article

References (26)

1. For a review see: Comasseto, J. V.; Petragnani, N. Synthesis 1991, 793 and 898.
2. a) Hiiro, T.; Mogami, T.; Kambe, N.; Fujiwara, S. I.; Sonoda, N. Angew. Chem. Int. Ed. Engl. 1987, 26, 1187.
3. b) Barros, S. M.; Dabdoub, M. J.; Dabdoub, V. B.; Comasseto, J. V. Organometallics 1989, 8, 1661.
4. c) Barros, S. M.; Comasseto, J. V.; Berriel, J. N. Tetrahedron Lett. 1989, 30, 7353.
5. d) Dabdoub, M. J.; Dabdoub, V. B.; Comasseto, J. V. Tetrahedron Lett. 1992, 33, 2261.
6. e) Ogawa, A.; Tsuboi, Y.; Obayashi, R.; Yokoyama, K.; Ryu, I.; Sonoda, N. J. Org. Chem. 1994, 59, 1600.
7. f) Mo, X. S.; Huang, Y. Z. Tetrahedron Lett. 1995, 36, 3539.
8. g) Dabdoub M. J.; Dabdoub, V. B. Tetrahedron 1995, 51, 9839.
9. h) Dabdoub, M. J.; Begnini, M. L.; Cassol, T. M.; Guerrero, P. G., Jr. Tetrahedron Lett. 1995, 36, 7623.
10. i) Dabdoub, M. J.; Cassol, T. M. Tetrahedron 1995, 51, 12971.
11. a) Tucci, F.; Chieffi, A.; Comasseto, J. V. Tetrahedron Lett. 1992, 33, 5121.
12. b) Marino, J. P.; Tucci, F.; Comasseto, J. V. Synlett 1993, 761.
13. c) Chieffi, A.; Comasseto, J. V. Tetrahedron Lett. 1994, 35, 4063.
14. Kanda, T.; Sugino, T.; Kambe, N.; Sonoda, N. Phosphorous, Sulfur and Silicon 1992, 67, 103.
15. Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; Wiley: New York, 1984.
16. Kent, J. L.; Wan, H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407 and references cited therein.
17. a) Nicolaou, K. C.; Maligres, P.; Shin, J.; de Leon, E.; Rideout, D. J. Amer. Chem. Soc. 1990, 112, 7825.
18. b) Andemichael, Y. W.; Gu, Y. G.; Wang, K. K. J. Org. Chem. 1992, 57, 794.
19. Hegedus, L. S.; Kambe, N.; Ishii, Y.; Mori, A. J. Org. Chem. 1985, 50, 2240.
20. Pourcelot, G.; Cadiot, P. Bull. Soc. Chim. France 1966, 3016.
21. Kanda, T.; Ando, Y.; Kato, S.; Kambe, N.; Sonoda, N. Synlett 1995, 745.
22. Dabdoub, M. J.; Dabdoub, V. B. to be published.
23. 12Te : C 37.57, H 5.41. Found : C 37.34, H 5.56.
24. 14Te : C 40.41, H 5.93. Found : C 40.16, H 6.08.
25. +).
26. 3) (60 MHz) 0.96 (t, J 7 Hz, 3H) 1.1-2.0 (m, 4H) 1.83 (t, J 2.2 Hz, 3H) 2.83 (t, J 7 Hz, 2H) 3.18 (q, J 2.2 Hz, 2H).