Addition of Z-vinylic higher order cyanocuprates to enones followed by O-functionalization

Tetrahedron

Volumn 56, Issue 21, 2000, Pages 3327-3337

  Moraes, D N ^a   Barrientos Astigarraga, R E ^a   Castelani, P ^a   Comasseto, J V ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Conjugated addition; Higher order cyanocuprates; Silyl enol ethers; Vinyl phosphates; Vinyl triflates; Z vinylic tellurides

Indexed keywords

COPPER DERIVATIVE; LITHIUM DERIVATIVE; TELLURIUM DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034685929     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00254-4     Document Type: Article

References (31)

1. For reviews see: (a) Comasseto, J. V. Rev. Hetereoatom. Chem. 1993, 9, 61. (b) Comasseto, J. V.; Ling, L. W.; Petragnani. N.; Stefani, H. A. Synthesis 1997, 373.
2. For reviews see: (a) Comasseto, J. V. Rev. Hetereoatom. Chem. 1993, 9, 61. (b) Comasseto, J. V.; Ling, L. W.; Petragnani. N.; Stefani, H. A. Synthesis 1997, 373.
3. (a) Barros, S. M.; Comasseto, J. V.; Dabdoub, M. J.; Dabdoub, V. B. Organometallics 1989, 8, 1661.
4. (b) Dabdoub, M. J.; Dabdoub, V. B.; Comasseto, J. V. Tetrahedron Lett. 1992, 33, 2261.
5. (c) Dabdoub, M. J.; Dabdoub, V. B. Tetrahedron 1995, 51, 9839.
6. Kauffmann T. Angew. Chem., Int. Ed. Engl. 94:1982;401.
7. Barros S.M., Comasseto J.V., Berriel J.N. Tetrahedron Lett. 30:1989;7353.
8. (a) Hiiro, T.; Kambe, N.; Ogawa, A.; Miyoshi, N.; Murai, S.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 1187.
9. (b) Kanda, T.; Sugino, T.; Kambe, N.; Sonoda, N. Phosphorus Sulfur Silicon Relat. Elem. 1992, 67, 103.
10. Tucci F., Chieffi A., Comasseto J.V., Marino J.P. J. Org. Chem. 61:1996;4975.
11. Wipf P. Synthesis. 1993;537.
12. Casson S., Kocienski P. Batesson J.H., Mitchell M.B. Organometallic Reagents in Organic Synthesis. Vol. 7:1994;129-159 Academic Press, London. (Chapter 7).
13. (a) Comasseto, J. V.; Berriel, J. Synth. Commun. 1990, 20, 1681.
14. (b) Tucci, F. C.; Chieffi. A.; Comasseto. J. V. Tetrahedron Lett. 1992, 33, 5721.
15. (c) Marino, J. P.; Tucci, F. C.; Comasseto, J. V. Synlett 1993, 1145.
16. (d) Araújo, M. A.; Barrientos-Astigarraga, R. E.; Ellensohn, R. M.; Comasseto, J. V. Tetrahedron Lett. 1999, 40, 5115.
17. Araújo M.A., Comasseto J.V. Synlett. 1995;1145.
18. Marino J.P., Simonelli F., Stengel P.J., Ferreira J.T.B. J. Braz. Chem. Soc. 9:1998;345. (and references cited therein).
19. (a) Ireland, R. E.; Pfister, G. Tetrahedron 1969, 2145.
20. (b) Muchmore, D. C. Org. Synth. 1972, 52, 109.
21. (c) Heathcock, C. H.; Delmar, E. G.; Graham, S. L. J. Am. Chem. Soc. 1982, 104, 1907.
22. Moorhoff C.M., Schneider D.F. Tetrahedron. 54:1998;3279. (and references cited therein).
23. For a review see: Ritter, K. Synthesis 1993, 8, 735.
24. Taylor R.J.K. Synthesis. 1985;364.
25. Lee K., Wiemer D.F. Tetrahedron Lett. 34:1993;2433.
26. Barrientos-Astigarraga R.E., Castelani P., Sumida C.Y., Comasseto J.V. Tetrahedron Lett. 40:1999;7717.
27. Barrientos-Astigarraga R.E., Moraes D.N., Comasseto J.V. Tetrahedron Lett. 40:1999;265.
28. Knochel P. Synlett. 1995;393.
29. Perrin D.D., Amarego W.L.F. Purification of Laboratory Chemicals. 2nd ed. 1980;Pergamon, London.
30. (a) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 39, 3839.
31. (b) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 46, 4607.