Direct Synthesis of Unprotected 4-Aryl Phenylalanines via the Suzuki Reaction under Microwave Irradiation

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3803-3805

  Gong, Yong ^a   He, Wei ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0041570557     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026587z     Document Type: Article

References (24)

1. Tilley, J. W.; Sidduri, A. Drugs Future 2001, 26, 985.
2. Firooznia, F.; Gude, C.; Chan, K.; Fink, A. C.; Qiao, Y.; Satoh, Y.; Marcopoulos, N.; Savage, P.; Beil, M. E.; Bruseo, C. W.; Trapani, A. J.; Jeng, A. Y. Bioorg. Med. Chem. Lett. 2001, 11, 375.
3. The Stille reaction has also been applied in the synthesis of N-Boc-4-aryl phenylalanine methyl esters: Morera, E.; Ortar, G. Synlett 1997, 1403.
4. (a) Shieh, W. C.; Carlson, J. A. J. Org. Chem. 1992, 57, 379.
5. (b) Burk, M. J.; Lee. J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847.
6. (c) Kotha, S.; Lahiri, K. Bioorg. Med. Chem. Lett. 2001, 11, 2887.
7. (a) Satoh, Y.; Gude, C.; Chan, K.; Firooznia, F. Tetrahedron Lett. 1997, 38, 7645.
8. (b) Firooznia, F.; Gude, C.; Chan, K.; Satoh, Y. Tetrahedron Lett. 1998, 39, 3985.
9. (c) Firooznia, F.; Gude, C.; Chan, K.; Marcopulos, N.; Satoh, Y. Tetrahedron Lett. 1999, 40, 213.
10. (a) Gong, Y.; Pauls, H. W. Synlett 2000, 829.
11. (b) Gong, Y.; Pauls, H. W.; Spada, A. P.; Czekaj, M.; Liang, G.; Chu, V.; Colussi, D. J.; Brown, K. D.; Gao, J. Bioorg. Med. Chem. Lett. 2000, 10, 217.
12. For recent reviews, see: (a) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
13. (b) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
14. (c) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95.
15. (d) Santagada, V.; Perissutti, E.; Caliendo, G. Curr. Med. Chem. 2002, 9, 1251.
16. +).
17. The reaction can be performed at higher concentration to (but not limited to) 2-mmol scale in the same vial, which broadens its preparative usefulness.
18. For the commentary of SmithSynthesizer, see: Watkins, K. J. Chem. Eng. News, 2002, 80 (6), 17.
19. 1,3-Dichloro-2-iodobenzene gave similar results to dichloro phenyl product 3d.
20. The coupling reaction can also be applied to 4-borono-D-phenylalanine. Both enantiomers are commercially available. For the preparation, see: (a) Malan, C.; Morin, C. J. Org. Chem. 1998, 63, 8019. (b) Nakamura, H.; Fujiwara, M.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000, 73, 231.
21. The coupling reaction can also be applied to 4-borono-D-phenylalanine. Both enantiomers are commercially available. For the preparation, see: (a) Malan, C.; Morin, C. J. Org. Chem. 1998, 63, 8019. (b) Nakamura, H.; Fujiwara, M.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000, 73, 231.
22. 3, 300 MHz) signals was observed with chemical shifts δ 4.95 (m, 1H) and 3.20 (s, 3H). Two sets of the corresponding signals were obtained at δ 5.05 (m, 1H), 4.95 (m, 1H), 3.40 (S, 3H), and 3.20 (s, 3H) for the Mosher's amides of racemic 3a.
23. (a) Bergmeier, S. C.; Ismail, K. A. Synthesis 2000, 1369.
24. (b) Rios, A.; Richard, J. P.; Amyes, T. L. J. Am. Chem. Soc. 2002, 124, 8251.