Direct Synthesis of Metal-Complexed Aromatic Amino Acid Derivatives by Palladium-Catalysed Coupling Processes

Synlett

Volumn 1996, Issue 9, 1996, Pages 862-864

  Jackson, Richard F W ^a   Turner, Debra ^a   Block, Michael H ^b  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002593859     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5612     Document Type: Article

References (18)

1. Schlögl, K. Monatsh. Chem. 1957, 88, 601-621; Osgerby, J.M.; Pauson, P.L. J. Chem. Soc. 1958, 656-660.
2. Schlögl, K. Monatsh. Chem. 1957, 88, 601-621; Osgerby, J.M.; Pauson, P.L. J. Chem. Soc. 1958, 656-660.
3. Pospísek, J.; Toma, S.; Fric, I.; Bláha, K. Coll. Czech. Chem. Comm. 1980, 45, 435-441.
4. Brunner, H; König, W.; Nuber, B. Tetrahedron:Asymmetry 1993, 4, 699-707.
5. Sergheraert, C.; Brunei, J.-C.; Tartar, A. J. Chem. Soc.,Chem. Commun. 1982, 1417-1418.
6. Jackson, R.F.W.; Wishart, N.; Wood, A.; James, K.; Wythes, M.J. J. Org. Chem., 1992, 57, 3397-3404.
7. Dunn, M.J.; Jackson, R.F.W.; Pietruszka, J.; Turner, D. J. Org. Chem. 1995, 60, 2210-2215.
8. Kovar, R.F.; Rausch, M.D.; Rosenberg, H. Organometal. Chem. Synth. 1970/1971, 1, 173-181.
9. Guillaneux, D.; Kagan, H.B. J. Org. Chem. 1995, 60, 2502-2505; and references therein.
10. We have carried out an X-ray crystal structure analysis of the ferrocenylalanine derivative 6 which allowed its absolute configuration to be confirmed: Clegg. W. and Elsegood, M.R.J.. Details will be published elsewhere.
11. Carlström, A.-S.; Frejd, T. J. Org. Chem. 1990, 55, 4175-4180.
12. Scott, W.J. J. Chem. Soc., Chem. Commun. 1987, 1755-1756; Clough, J.M.; Mann, I.S.; Widdowson, D.A. Tetrahedron Lett. 1987, 28, 2645-2648. See also: Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375-1384, and references therein.
13. Scott, W.J. J. Chem. Soc., Chem. Commun. 1987, 1755-1756; Clough, J.M.; Mann, I.S.; Widdowson, D.A. Tetrahedron Lett. 1987, 28, 2645-2648. See also: Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375-1384, and references therein.
14. Scott, W.J. J. Chem. Soc., Chem. Commun. 1987, 1755-1756; Clough, J.M.; Mann, I.S.; Widdowson, D.A. Tetrahedron Lett. 1987, 28, 2645-2648. See also: Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375-1384, and references therein.
15. The tricarbonylchromium complexes were prepared by refluxing a solution of the corresponding arene in di-n-butyl ether and THF (10:1) containing hexacarbonylchromium, under nitrogen. A long condenser, with a cooling coil in the top half only, ensured that sublimed hexacarbonylchromium was returned to the reaction vessel. See, for example: Ghavshou, M.; Widdowson, D.A. J. Chem. Soc., Perkin Trans. 1 1983, 3065-3070.
16. 2). Complexes 10b and 10e were isolated as diastereoisomeric mixtures, and the reported integrals refer to each individual diastereoisomer.
17. 4
18. Block, M.H.; Jackson, R.F.W.; Turner, D. unpublished results.