Efficient synthesis of protected β-phenylethylamines, enantiomerically pure protected β-phenyl-α-benzylethylamines and β-phenyl-α-isopropylethylamines using organozinc chemistry

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 2, 2000, Pages 219-223

  Hunter, Christopher ^a   Jackson, Richard F W ^a   Rami, Harshad K ^b  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINO ACIDS; CATALYSIS; PALLADIUM; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ORGANOZINC CHEMISTRY;

AMINES;

EID: 0034695707     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907629h     Document Type: Article

References (23)

1. R. F. W. Jackson, N. Wishart, A. Wood, K. James and M. J. Wythes, J. Org. Chem., 1992, 57, 3397.
2. M. J. Dunn, R. F. W. Jackson, J. Pietruszka and D. Turner, J. Org. Chem., 1995, 60, 2210.
3. R. F. W. Jackson, R. J. Moore, C. S. Dexter, J. Elliott and C. E. Mowbray, J. Org. Chem., 1998, 63, 7875.
4. C. S. Dexter and R. F. W. Jackson, Chem. Commun., 1998, 75.
5. G. A. Cordell, Introduction to Alkaloids-A Biogenic Approach, Wiley, New York, 1981.
6. D. E. Nichols, S. E. Synder, R. Oberlander, M. P. Johnson and X. Haung, J Med. Chem., 1991, 34, 276.
7. F. Claudi, M. Cardellini, G. M. Cingolani, A. Piergentilli, P. Guidubaldo and W. Balduini, J. Med. Chem., 1990, 33, 2408.
8. H. F. Bradford, Chemical Neurobiology, Freeman, New York, 1986.
9. K. W. Bentley, Nat. Prod. Rep., 1998, 15, 341.
10. Z. Zhuangyu, P. Yi, H. Hongwen and T. Kao, Synth. Commun., 1990, 20, 3563.
11. C. A. Busacca, R. E. Johnson and J. Swestock, J. Org. Chem., 1993, 58, 3299.
12. M. J. Eis and B. Ganem, Tetrahedron Lett., 1985, 26, 1153.
13. J. Barluenga, F. Foubela, F. J. Fañanás and M. Yus, Tetrahedron, 1989, 45, 2183.
14. J. A. Sejas, M. P. Vasquez-Tato, C. Entanza and M. M. Martinez, Tetrahedron Lett., 1998, 39, 5073.
15. R. Duddu, M. Eckhardt, M. Furlong, H. P. Knoess, S. Berger and P. Knochel, Tetrahedron, 1994, 50, 2415.
16. G. L. Lange and C. Gottardo, Synth. Commun., 1990, 20, 1473.
17. P. Knochel and R. D. Singer, Chem. Rev., 1993, 93, 2117.
18. P. G. Mattingly, Synthesis, 1990, 366.
19. A. W. Konradi, S. J. Kemp and S. F. Pedersen, J. Am. Chem. Soc., 1994, 116, 1316.
20. A. M. Doherty, J. S. Kaltenbronn, J. P. Hudspeth, J. T. Repine, W. H. Roark, I. Sircar, F. J. Tinney, C. J. Connolly, J. C. Hodges, M. D. Taylor, B. L. Batley, M. J. Ryan, A. D. Essenburg, S. T. Rapundalo, R. E. Weishaar, C. Humblet and E. A. Lunney, J. Med. Chem., 1991, 34, 1258.
21. R. Caputo, E. Cassano, L. Longobardo and G. Palumbo, Tetrahedron Lett., 1995, 36, 167.
22. K. Ninomiya, J. Med. Chem., 1974, 30, 2151.
23. P. A. Stark, B. D. Thrall, G. G. Meadows and M. M. Abdel-Monem, J. Med Chem., 1992, 35, 4264.