Electrophilic substitutions of 1-alkenylcyclopropyl esters: Diethylzinc- mediated umpolung of π-1,1-dimethyleneallyl palladium complexes

Synlett

Volumn , Issue 10, 1999, Pages 1539-1542

  Ollivier, Jean ^a   Girard, Nicolas ^a   Salaün, Jacques ^a  

^a CNRS   (France)

Author keywords

1,1 Dimethyleneallyl zinc complexes; 3 cyclopropylidenepropan 1ols; Regioselective and electrophilic substitutions

Indexed keywords

CYCLOPROPANE DERIVATIVE; ESTER DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; FRANCE; SYNTHESIS;

EID: 0032861738     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2883     Document Type: Article

References (42)

1. Salaün, J.; Baird, M.S. Curr. Med. Chem. 1995, 2, 511-542; Salaün, J. Top. Curr. Chem. 1999, in press.
2. Salaün, J.; Baird, M.S. Curr. Med. Chem. 1995, 2, 511-542; Salaün, J. Top. Curr. Chem. 1999, in press.
3. Salaün, J. Rearrangements involving the Cyclopropyl Group. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987, p. 809-878; Small Ring Compounds in Organic Synthesis I-VI; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, 1986, Vol. 133; 1987, Vol. 135; 1988, Vol. 144; 1990, Vol. 155; 1996, Vol. 178; 1999, Vol. in press; Carbocyclic Three and Four-membered Ring Systems. Houben-Weyl: Methods of Organic Chemistry. de Meijere, A. Ed.; Thieme Stuttgart, 1997, Vol. E 17a-f.
4. Salaün, J. Rearrangements involving the Cyclopropyl Group. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987, p. 809-878; Small Ring Compounds in Organic Synthesis I-VI; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, 1986, Vol. 133; 1987, Vol. 135; 1988, Vol. 144; 1990, Vol. 155; 1996, Vol. 178; 1999, Vol. in press; Carbocyclic Three and Four-membered Ring Systems. Houben-Weyl: Methods of Organic Chemistry. de Meijere, A. Ed.; Thieme Stuttgart, 1997, Vol. E 17a-f.
5. Salaün, J. Rearrangements involving the Cyclopropyl Group. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987, p. 809-878; Small Ring Compounds in Organic Synthesis I-VI; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, 1986, Vol. 133; 1987, Vol. 135; 1988, Vol. 144; 1990, Vol. 155; 1996, Vol. 178; 1999, Vol. in press; Carbocyclic Three and Four-membered Ring Systems. Houben-Weyl: Methods of Organic Chemistry. de Meijere, A. Ed.; Thieme Stuttgart, 1997, Vol. E 17a-f.
6. Salaün, J. Rearrangements involving the Cyclopropyl Group. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987, p. 809-878; Small Ring Compounds in Organic Synthesis I-VI; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, 1986, Vol. 133; 1987, Vol. 135; 1988, Vol. 144; 1990, Vol. 155; 1996, Vol. 178; 1999, Vol. in press; Carbocyclic Three and Four-membered Ring Systems. Houben-Weyl: Methods of Organic Chemistry. de Meijere, A. Ed.; Thieme Stuttgart, 1997, Vol. E 17a-f.
7. Salaün, J. Rearrangements involving the Cyclopropyl Group. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987, p. 809-878; Small Ring Compounds in Organic Synthesis I-VI; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, 1986, Vol. 133; 1987, Vol. 135; 1988, Vol. 144; 1990, Vol. 155; 1996, Vol. 178; 1999, Vol. in press; Carbocyclic Three and Four-membered Ring Systems. Houben-Weyl: Methods of Organic Chemistry. de Meijere, A. Ed.; Thieme Stuttgart, 1997, Vol. E 17a-f.
8. Salaün, J. Rearrangements involving the Cyclopropyl Group. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987, p. 809-878; Small Ring Compounds in Organic Synthesis I-VI; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, 1986, Vol. 133; 1987, Vol. 135; 1988, Vol. 144; 1990, Vol. 155; 1996, Vol. 178; 1999, Vol. in press; Carbocyclic Three and Four-membered Ring Systems. Houben-Weyl: Methods of Organic Chemistry. de Meijere, A. Ed.; Thieme Stuttgart, 1997, Vol. E 17a-f.
9. Salaün, J. Rearrangements involving the Cyclopropyl Group. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987, p. 809-878; Small Ring Compounds in Organic Synthesis I-VI; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, 1986, Vol. 133; 1987, Vol. 135; 1988, Vol. 144; 1990, Vol. 155; 1996, Vol. 178; 1999, Vol. in press; Carbocyclic Three and Four-membered Ring Systems. Houben-Weyl: Methods of Organic Chemistry. de Meijere, A. Ed.; Thieme Stuttgart, 1997, Vol. E 17a-f.
10. Salaün, J. Rearrangements involving the Cyclopropyl Group. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987, p. 809-878; Small Ring Compounds in Organic Synthesis I-VI; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, 1986, Vol. 133; 1987, Vol. 135; 1988, Vol. 144; 1990, Vol. 155; 1996, Vol. 178; 1999, Vol. in press; Carbocyclic Three and Four-membered Ring Systems. Houben-Weyl: Methods of Organic Chemistry. de Meijere, A. Ed.; Thieme Stuttgart, 1997, Vol. E 17a-f.
11. a) Ainsworth, C.; Chen, F.; Kuo, Y.-N. J. Organomet. Chem. 1972, 46, 59-71;
12. b) Häner, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1655-1665;
13. c) Brückner, C.; Reissig, H.-U. J. Org. Chem. 1988, 53, 2440-2450.
14. Braun, M.; Seebach, D. Angew. Chem. 1974, 86, 279-280; Angew. Chem. Int. Ed. Engl. 1974, 13, 277-278; Braun, M.; Dammann, R.; Seebach, D. Chem. Ber. 1975, 109, 2368-2390.
15. Braun, M.; Seebach, D. Angew. Chem. 1974, 86, 279-280; Angew. Chem. Int. Ed. Engl. 1974, 13, 277-278; Braun, M.; Dammann, R.; Seebach, D. Chem. Ber. 1975, 109, 2368-2390.
16. Braun, M.; Seebach, D. Angew. Chem. 1974, 86, 279-280; Angew. Chem. Int. Ed. Engl. 1974, 13, 277-278; Braun, M.; Dammann, R.; Seebach, D. Chem. Ber. 1975, 109, 2368-2390.
17. Trost, B.M. Top. Curr. Chem. 1986, 133, 3-82.
18. Krief, A. Top. Curr. Chem. 1987, 135, 1-75.
19. Gadwood, R.C.; Rubino, M.R.; Nagarajan, S.C.; Michel, S.T. J. Org. Chem. 1985, 50, 3255-3260.
20. Wells, G.J.; Yan, T.H.; Paquette, L.A. J. Org. Chem. 1984, 49, 3604-3609; Paquette, L.A.; Yan, T.H.; Wells, G.J. J. Org. Chem. 1984, 49, 3610-3617; Paquette, L.A.; Wells, G.J.; Wickham, G. J. Org. Chem. 1984, 49, 3618-3621.
21. Wells, G.J.; Yan, T.H.; Paquette, L.A. J. Org. Chem. 1984, 49, 3604-3609; Paquette, L.A.; Yan, T.H.; Wells, G.J. J. Org. Chem. 1984, 49, 3610-3617; Paquette, L.A.; Wells, G.J.; Wickham, G. J. Org. Chem. 1984, 49, 3618-3621.
22. Wells, G.J.; Yan, T.H.; Paquette, L.A. J. Org. Chem. 1984, 49, 3604-3609; Paquette, L.A.; Yan, T.H.; Wells, G.J. J. Org. Chem. 1984, 49, 3610-3617; Paquette, L.A.; Wells, G.J.; Wickham, G. J. Org. Chem. 1984, 49, 3618-3621.
23. Stolle, A.; Ollivier, J.; Piras, P.P.; Salaün, J.; de Meijere, A. J. Am. Chem. Soc. 1992, 114, 4051-4067.
24. Salaün, J. J. Org. Chem. 1976, 41, 1237-1240; Salaün, J. Chem. Rev. 1983, 83, 619-632.
25. Salaün, J. J. Org. Chem. 1976, 41, 1237-1240; Salaün, J. Chem. Rev. 1983, 83, 619-632.
26. Estieu, K.; Paugam, R.; Ollivier, J.; Salaün, J.; Cordero, F.M.; Goti, A.; Brandi, A. J. Org. Chem. 1997, 62, 8276-8277; Ferrara, M.; Cordero, F.M.; Goti, A.; Brandi, A.; Estieu, K.; Paugam, R.; Ollivier, J.; Salaün, J. Eur. J. Org. Chem. 1999, in press.
27. Estieu, K.; Paugam, R.; Ollivier, J.; Salaün, J.; Cordero, F.M.; Goti, A.; Brandi, A. J. Org. Chem. 1997, 62, 8276-8277; Ferrara, M.; Cordero, F.M.; Goti, A.; Brandi, A.; Estieu, K.; Paugam, R.; Ollivier, J.; Salaün, J. Eur. J. Org. Chem. 1999, in press.
28. Aufranc, P. Ollivier, J.; Stolle, A.; Bremer, C.; Es-Sayed, M.; de Meijere, A.; Salaün, J. Tetrahedron Lett. 1993, 34, 4193-4196.
29. Keinen, E.; Bosch, E. J. Org. Chem. 1986, 51, 4006-4016.
30. Ollivier, J.; Piras, P.P.; Stolle, A.; Aufranc, P.; de Meijere, A.; Salaün, J. Tetrahedron Lett. 1992, 33, 3307-3310; Ollivier, J.; Dorizon, Ph.; Piras, P.P.; de Meijere, A.; Salaün, J. Inorg. Chim. Acta 1994, 222, 37-49.
31. Ollivier, J.; Piras, P.P.; Stolle, A.; Aufranc, P.; de Meijere, A.; Salaün, J. Tetrahedron Lett. 1992, 33, 3307-3310; Ollivier, J.; Dorizon, Ph.; Piras, P.P.; de Meijere, A.; Salaün, J. Inorg. Chim. Acta 1994, 222, 37-49.
32. Atlan, V.; Racouchot, S.; Rubin, M.; Bremer, C.; Ollivier, J.; de Meijere, A.; Salaün, J. Tetrahedron: Asymmetry 1998, 9, 1131-1135.
33. Menningen, P.; Harcken, C.; Stecker, B.; Körbe, S.; de Meijere, A.; Lopes, M.; Ollivier, J.; Salaün, J. Synlett 1999, 1534.
34. Kasatkin, A.; Sato, F. Angew. Chem. 1996, 108, 3024-3025; Angew. Chem. Int. Ed. Engl. 1996, 35, 2848-2849.
35. Kasatkin, A.; Sato, F. Angew. Chem. 1996, 108, 3024-3025; Angew. Chem. Int. Ed. Engl. 1996, 35, 2848-2849.
36. a) Yasui, K.; Goto, Y.; Yajima, T.; Taniseki, Y.; Fugami, K.; Tanaka, A.; Tamaru, Y. Tetrahedron Lett. 1993, 34, 7619-7622;
37. b) Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem. Int. Ed. Engl. 1995, 34, 787-789;
38. c) Shimizu, M.; Kimura, M.; Tanaka, S.; Tamaru, Y. Tetrahedron Lett. 1998, 39, 609-612;
39. d) Kimura, M.; Ogawa, Y.; Shimizu, M.; Sueishi, M.; Tanaka, S.; Tamaru, Y. Tetrahedron Lett. 1998, 39, 6903-6906.
40. 28OSi: 288.19093 ).
41. Cuvigny, T.; Julia, M.; Rolando, C. J. Organomet. Chem. 1985, 285, 395-413.
42. Bertrand, M.; Leandri, G.; Meou, A. Tetrahedron 1981, 37, 1703-1710.