Palladium catalysed mono-N-arylation of enantiopure diamines

Tetrahedron Asymmetry

Volumn 10, Issue 10, 1999, Pages 1831-1834

  Frost, Christopher G ^a   Mendonça, Paul ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE; DIAMINE; LIGAND;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROGENATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0033591119     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00158-5     Document Type: Article

References (15)

1. Noyori, R. Asymmetric Catalysis in Organic Synthesis. John Wiley & Sons: New York, 1994.
2. Pospil, P. J.; Carsten, D. H.; Jacobsen, E. N. Chem. Eur. J. 1996, 2, 974.
3. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089.
4. Ohkuma, T.; Doucet, H.; Pham, T.; Mikami, K.; Korenaga, T.; Terada, M.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 1086.
5. (a) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
6. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
7. (c) For a recent review, see: Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615.
8. Frost, C. G.; Mendonça, P. Chem. Lett. 1997, 1159.
9. Wagaw, S.; Rennels, R. A.; Buchwald S. L. J. Am. Chem. Soc. 1997, 119, 8451.
10. For previous work on the catalytic amination of polyamines, see: Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Tetrahedron Lett. 1997, 38, 2287.
11. All new compounds have been fully characterised and show satisfactory analytical data. The enantiopurity of all the mono-N-arylated products was >95% (NMR of Mosher's amide).
12. For a full account, see: Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
13. Püntener, K.; Schwink, L.; Knochel, P. Tetrahedron Lett. 1996, 37, 8165.
14. For a typical procedure, see: Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562.
15. Hashiguchi, S.; Fujii, A.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521.