Memory effects in Pd-catalyzed allylic alkylations

Chemtracts

Volumn 12, Issue 11, 1999, Pages 837-845

  Lloyd Jones, G C ^b   Stephen, B C ^b   Trost, B M ^b   Bunt, R C ^b  

^a UNIVERSITY OF FLORENCE   (Italy)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; PALLADIUM COMPLEX;

ALKYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; REVIEW; STEREOCHEMISTRY;

EID: 0032744795     PISSN: 14319268     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (18)

1. See the preceding article in this issue.
2. Fiaud, J.C., Malleron, J.L. Tetrahedron Lett. 1981, 22, 1399.
3. Trost, B.M., Schmuff, N.R. Tetrahedron Lett. 1981, 22, 2999.
4. Trost, B.M., Bunt, R.C. J. Am. Chem. Soc. 1996, 118, 235.
5. Trost, B.M., Van Vranken, D.L., Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327.
6. If the two chiral ligands are viewed along their extended backbone, one can assign a counterclockwise twist to ligand (R,R)-L, and a clockwise twist to ligand (S,S)-L. Then, according to a mnemonic proposed by the authors, viewing the substrate in the plane of the paper with the leaving groups below the plane of the paper, and the metal above the plane, correlation exists between the twist of the ligand and the motion of the metal with respect to the substrate.
7. Lloyd-Jones, G.C., Stephen, S.C. Chem. Eur. J. 1998, 4, 2539.
8. 2H-isotope shifts and paramagnetic diastereo-topic shifts has been used.
9. Oare, D.A., Heathcock, C.H. Top. Stereochem. 1989, 19, 227.
10. X-ray crystallographic evidence has been obtained for such a coordination. Lloyd-Jones, G.C. Personal communication.
11. The chloride ion appears to coordinate to Pd(0).
12. Lloyd-Jones, G.C., Stephen, S.C. J. Chem. Soc. Chem. Commun. 1998, 2321.
13. Kocovský, P., Vyskocil, Š., Císarová, I., Srjbal, J., Tišlerova, I., Smrcina, M., Lloyd-Jones, G.C., Stephen, S.C., Butts, C.P., Murray, M., Langer, V. J. Am. Chem. Soc. 1999, 121, 7714.
14. Trost, B.M. Acc. Chem. Res. 1996, 29, 355.
15. (a) Steinhagen, H., Reggelin, M., Helmchen, G. Angew. Chem. Int. Ed. Engl. 1997, 36, 2108
16. (b) Brown, J.M., Hulmes, D.J., Guiry, P.J. Tetrahedron 1994, 50, 4493
17. (c) Knühl, G., Sennhenn, P., Helmchen, G. J. Chem. Soc. Chem. Commun. 1995, 1845
18. (d) Helmchen, G., Kudis, S., Sennhen, P. Pure Appl. Chem. 1997, 69, 513.