The synthesis of novel amino acids via hydroboration-suzuki cross coupling

Tetrahedron Letters

Volumn 40, Issue 28, 1999, Pages 5263-5266

  Campbell, Andrew D ^a   Raynham, Tony M ^b   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE DERIVATIVE; AMINO ACID DERIVATIVE; ORGANOBORON DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; OXIDATION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

LATEOLABRAX JAPONICUS;

EID: 0033538668     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00997-1     Document Type: Article

References (21)

1. Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: Oxford, 1989; For recent reviews see Jackson, R. F. W.; Moore, R. J.; Dexter, C. S.; Elliot, J.; Mowbray. C. E. J. Org. Chem., 1998, 63, 7875-7884; Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854 and references therein.
2. Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: Oxford, 1989; For recent reviews see Jackson, R. F. W.; Moore, R. J.; Dexter, C. S.; Elliot, J.; Mowbray. C. E. J. Org. Chem., 1998, 63, 7875-7884; Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789 -12854 and references therein.
3. Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854 and references therein.
4. For our own work in this area see (a) Guo, Z.-X.; Schaeffer, M. J.; Taylor, R. J. K. Taylor Chem Commun. 1993, 874-875;
5. (b) Baxter, A. D.; Murray, P. J.; Taylor, R. J. K. Tetrahedron Lett., 1992, 33, 2331-2334.
6. (a) Wittig approaches: see reference 2b and Beaulieu, P. L.; Duceppe, J.-S.; Johnson, C. J. Org. Chem. 1991, 56, 4196-4204;
7. (b) Via Alkynylation: Meffre, P.; Gauzy, L.; Banquet, E.; Durand, P.; Le Goffic, F. Tetrahedron 1996, 52, 11212-11238;
8. Reginato, G.; Mordini, A.; Caracciolo, M. J. Org. Chem. 1997, 62, 6187-6192;
9. (c) Organometallic additions: Bold, G.; Alimendinger, T.; Herold, P.; Moesch, L.; Schär, H.-P.; Duthaler, R. O. Helv. Chim. Acta 1992, 75, 865-882.
10. Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. Chem Commun. 1999, 245-246.
11. Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709;
12. McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. Synthesis 1994, 31-33.
13. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483;
14. (b) Miyaura, N.; Ishiyama, T.; Sasaki, H; Ishikawa, M.; Satoh, M.; Suzuki A. J. Am. Chem. Soc. 1989, 111, 314-321;
15. (c) Johnson, C. R.; Johns, B. A. Synlett 1997, 1406-1408.
16. Donloni, A.; Marra, A.; Massi, A. Tetrahedron 1998, 54, 2827-2832.
17. We subsequently discovered that the hydroboration studies, but not the iodination or coupling reactions, have been reported: Kawate. T.; Fukata, N.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1997, 45, 2116-2118.
18. All new compounds were fully characterized by high field NMR spectroscopy and by HRMS.
19. 4) nd the solvent in vacuo. Purification by flash chromatography on silica (light petrolium-ethyl acetate) gave the product (53mg. 79%) as a white *tabyflasbchtQmatfl
20. Jackson, R. F. W.; Fraser, J. L.; Wishart, N.; Porter. B.; Wythes, M. J. J. Chem. Soc. Perkin Trans. 1 1998, 12, 1903-1912.
21. Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen. D. J. Am. Chem. Soc. 1988, 110, 1547-1557.