Palladium Catalysed Asymmetric Allylic Substitution. Routes to β-Amino Acids

Synlett

Volumn 1996, Issue 7, 1996, Pages 685-686

  Bower, Justin F ^a   Williams, Jonathan M J ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002764426     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5560     Document Type: Article

References (17)

1. (a) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichimica Acta 1994, 27, 3.
2. (b) Cole D. C. Tetrahedron 1994, 50, 9517.
3. (a) Auburn, P. R.; MacKenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033.
4. (b) MacKenzie, P. B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046.
5. (c) Togni, A. Tetrahedron: Asymmetry 1991, 2, 683.
6. (d) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493.
7. This ligand has been independently prepared by other researchers and successfully employed in other palladium catalysed allylic substitution reactions. (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149.
8. This ligand has been independently prepared by other researchers and successfully employed in other palladium catalysed allylic substitution reactions. (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149.
9. This ligand has been independently prepared by other researchers and successfully employed in other palladium catalysed allylic substitution reactions. (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149.
10. (a) Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1995, 36, 461.
11. (b) Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry 1995, 6, 2535.
12. (a) Krapcho, A. P. Synthesis 1982, 805, 893.
13. (b) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuberger, M.; Zehnder, M.; Reugger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265.
14. (a) Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203.
15. (b) Eaton, P. E.; Ravi Shankar, B. K. J. Org. Chem. 1984, 49, 185.
16. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
17. 2O), Balenovic, K.; Bregant, N. Tetrahedron 1959, 5, 44. A Chiralcel OD column was employed for the analytical resolution of compounds 8b-d, using iPrOH/hexane (20:80) as the eluent (For compound 8b, the iPrOH also contained 5% TFA)