Bis(aminophosphine)-nickel complexes as efficient catalysts for alkylation of allylic acetates with stabilized nucleophiles

Tetrahedron Letters

Volumn 37, Issue 34, 1996, Pages 6105-6108

  Bricout, Hervé ^a   Carpentier, Jean François ^a   Mortreux, André ^a  

^a Ecole Nationale Superieure de Chimie de Lille   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; NICKEL; PHOSPHINE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYST; CHIRALITY; COMPLEX FORMATION; DRUG ACTIVITY; DRUG STABILITY; LIGAND BINDING; NONHUMAN;

EID: 0030593614     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01302-0     Document Type: Article

References (32)

1. 1. Jolly, P. W.; Wilke, G. in The Organic Chemistry of Nickel, Academic Press: Orlando, FL, 1975, Vol. II, 147-193.
2. 2. For leading references see: (a) Chuit, C.; Felkin, H.; Frajerman, C.; Roussi, G.; Swierczewski, G. J. Chem. Soc., Chem. Commun. 1968, 1604-1605.
3. (b) Cherest, M.; Felkin, H.; Umpleby, J. D.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1981, 681-682.
4. (c) Consiglio, G.; Morandini, F.; Piccolo, O. J. Am. Chem. Soc. 1981, 103, 1846-1847.
5. (d) Consiglio, G.; Piccolo, O.; Roncetti, L.; Morandini, F. Tetrahedron 1986, 42, 2043-2053.
6. (e) Kobayashi, Y.; Ikeda, E. J. Chem. Soc., Chem. Commun. 1994, 1789-1790.
7. (f) Consiglio, G.; Waymouth, R. Chem. Rev. 1989, 89, 257-276.
8. 3. (a) Furukawa, J.; Kiji, J.; Yamamoto, K.; Tojo, T. Tetrahedron 1973, 29, 3149-3151.
9. (b) Yamamoto, T.; Ishizu, J.; Yamamoto, A. J. Am. Chem. Soc. 1981, 103, 6863-6869.
10. (c) Cuvigny, T.; Julia, M. J. Organomet. Chem. 1983, 250, C21-C24.
11. (d) ibid, 1986, 317, 383-408.
12. (e) Alvarez, E.; Cuvigny, T.; Julia, M. J. Organomet. Chem. 1988, 339, 199-212.
13. 4. (a) Trost, B. M.; Verhoeven, T. R. in Comprehensive Organometallic Chemistry; G. Wilkinson, Ed.; Pergamon: Oxford, U.K., 1982, pp 799-938.
14. (b) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
15. (c) Tsuji, J. Tetrahedron, 1986, 42, 4361.
16. (d) Trost, B. M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1173-1192.
17. (e) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122.
18. (f) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
19. 5. Bricout, H.; Carpentier, J.-F.; Mortreux, A. J. Chem. Soc., Chem. Commun. 1995, 1863-1864.
20. 6. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145.
21. 7. For the synthesis of bis(N-methyl-N-diphenylphosphinoamino)-1,2-ethane (dppmae), see: Grimblot, J.; Bonnelle, J.-P.; Vaccher, C.; Mortreux, A.; Petit, F.; Peiffer, G. J. Mol. Catal. 1980, 9, 357-368.
22. 8. A rapid catalyst poisoining (ca 5 min.) with a concomitant stoichiometric production of isoprene and acetic acid with respect to nickel was observed (overall conversion of 1,1-dimethylallyl acetate ∼ 1%).
23. 9. To the best of our knowledge, only examples of nickel-catalysed asymmetric akylations with non stabilized nucleophiles have been reported so far; see references 2b, 2d, 2f, 4f.
24. 10. Roucoux, A.; Suisse, I.; Devocelle, M.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A. Tetrahedron: Asymmetry 1996, 7, 379-382.
25. 11. (a) Agbossou, F.; Carpentier, J.-F.; Hatat, C.; Kokel, N.; Mortreux, A.; Betz, P.; Goddard, R.; Krüger, C. Organometallics 1995, 14, 2480-2489.
26. (b) Roucoux, A.; Thieffry, L.; Carpentier, J.-F.; Devocelle, M.; Meliet, C.; Agbossou, F.; Mortreux, A.; Welch, A. J. Organometallics 1996, 15, 2440-2449.
27. 12. (a) 50% ee: Togni, A. Tetrahedron: Asymmetry 1991, 2, 683-690.
28. (b) 54% ee: Sennhenn, P.; Gabler, B.; Helmchen, G. Tetrahedron Lett. 1994, 35, 8595-8596.
29. (c) 62% ee: Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352.
30. (d) 67% ee: Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506.
31. 2 symmetry diphosphine and a tetraalkylammonium salt: Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090.
32. (f) 98% ee obtained with a new heterobidentate P,O-ligand: Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845-1846.