Asymmetric and efficient synthesis of homophenylalanine derivatives via Friedel-Crafts reaction with trifluoromethanesulfonic acid

Tetrahedron Letters

Volumn 49, Issue 46, 2008, Pages 6566-6568

  Murashige, Ryo ^a   Hayashi, Yuka ^a   Hashimoto, Makoto ^a  

^a OBIHIRO UNIVERSITY OF AGRICULTURE AND VETERINARY MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE DERIVATIVE; AROMATIC COMPOUND; BENZENE; HOMOPHENYLALANINE; SOLVENT; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; FRIEDEL CRAFTS REACTION; STOICHIOMETRY;

EID: 52949135143     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.013     Document Type: Article

References (28)

1. Mosberg H.I., Heyl D.L., Haaseth R.C., Omnaas J.R., Medzihradsky F., and Smith C.B. Mol. Pharmacol. 38 (1990) 924
2. Abiko T., and Sekino H. Drug Dev. Ind. Pharm. 24 (1998) 569
3. Chang C.Y., and Yang T.K. Tetrahedron: Asymmetry 14 (2003) 2081
4. Chang C.Y., and Yang T.K. Tetrahedron: Asymmetry 14 (2003) 2239
5. Zhao H., Luo R.G., Wei D., and Malhotra S.V. Enantiomer 7 (2002) 1
6. Barfoot C.W., Harvey J.E., Kenworthy M.N., Kilburn J.P., Ahmed M., and Taylor R.J.K. Tetrahedron 61 (2005) 3403
7. Yamada M., Nagashima N., Hasegawa J., and Takahashi S. Tetrahedron Lett. 39 (1998) 9019
8. Xie Y., Lou R., Li Z., Mi A., and Jiang Y. Tetrahedron: Asymmetry 11 (2000) 1487
9. Reifenrath W.G., Bertelli D.J., Micklus M.J., and Fries D.S. Tetrahedron Lett. 17 (1976) 1959
10. Nordlander J.E., Payne M.J., Njoroge F.G., Vishwanath V.M., Han G.R., Laikos G.D., and Balk M.A. J. Org. Chem. 50 (1985) 3619
11. Melillo D.G., Larsen R.D., Mathre D.J., Shukis W.F., Wood A.W., and Colleluori J.R. J. Org. Chem. 52 (1987) 5143
12. Griesbeck A.G., and Heckroth H. Synlett (1997) 1243
13. Lin W., He Z., Zhang H., Zhang X., Mi A., and Jiang Y. Synthesis 7 (2001) 1007
14. Xu Q., Wang G., Wang X., Wu T., Pan X., Chan A.S.C., and Yang T. Tetrahedron: Asymmetry 11 (2000) 2309
15. Weygand F., Klinke P., and Eigen I. Chem. Ber. 90 (1957) 1896
16. 7a.
17. Katrizky A.R., Tao H., Jiang R., Suzuki K., and Kirichenko K. J. Org. Chem. 72 (2007) 407
18. Effenberger F., and Epple G. Angew. Chem., Int. Ed. Engl. 11 (1972) 299
19. Germain A., and Commeyras A. J. Chem. Soc., Chem. Commun. 24 (1972) 1345
20. Hwang J.P., Prakash G.K.S., and Olah G.A. Tetrahedron 56 (2000) 7199
21. Khodaei M.M., Alizadeh A., and Nazari E. Tetrahedron Lett. 48 (2007) 4199
22. Ariyoshi Y., Yamatani T., Uchiyama N., and Sato N. Bull. Chem. Soc. Jpn. 45 (1972) 2208
23. Svete J., and Stanocnik B. J. Heterocycl. Chem. 31 (1994) 1259-1266
24. 4, then filtrated. The filtrate was concentrated to afford a F-C product.
25. Kirk K.L. J. Org. Chem. 45 (1980) 2015
26. Petasis N.A., and Zavialov I.A. J. Am. Chem. Soc. 119 (1997) 445
27. Long A., and Baldwin S.W. Tetrahedron Lett. 42 (2001) 5343
28. Sabat M., and Johnson C.R. Org. Lett. 2 (2000) 1089