An Efficient Method for the Reduction of N-Protected Amino Acids and Peptides to the Corresponding Alcohols

Abstract

Reduction of pentachlorophenyl esters of Boc protected amino acids and peptides to the corresponding alcohols is described.

References

1. C. F. Stanfield, J. E. Parker and J. Kanellis, J. Org. Chem., 1981, 46, 4797.
2. H. Umezawa, Methods Enzymol., 1976, 45, 678.
3. J. Martinez, J. P. Bali, M. Rodriguez, B. Castro, R. Mayous, J. Laur and M. F. Lignon, J. Med. Chem., 1985, 28, 1874.
4. R. E. TenBrutk, J. Org. Chem., 1987, 52, 418.
5. C. Bolm, Angew. Chem., Int. Ed. Engl., 1991, 30, 542.
6. C. Aurin-Guette, S. Rebuffat, Y. Prigent and B. Bodo, J. Am. Chem. Soc., 1992, 114, 2170; C. I. Fincham, M. Higginbottom, D. R. Hill, D. C. Horwell, J. C. O'Toole, G. S. Ratcliffe, D. C. Rees and E. Roberts, J. Med. Chem., 1992, 35, 1472.
7. T. Sawayama, M. Tsukamoto, T. Sasagawa, S. Naruto, J. Matsumoto and H. Uno, Chem. Pharm. Bull., 1989, 37, 1382; M. Kawai, Y. Omori, H. Yamamura and Y. Butsagan, Tetrahedron: Asymmetry, 1992, 3, 1010.
8. S. Wu, R. Takeya, M. Eto and C. Tomizawa, J. Pestic. Sci., 1979, 12, 221.
9. P. Karrer, W. Karrer, H. Thomann, E. Horlacher and W. Mader, Helv. Chim. Acta., 1921, 4, 76.
10. P. Karrer and M. Suter, Helv. Chim. Acta., 1948, 32, 1156.
11. H. Seki, K. Koga, H. Matsuo, S. Ohiki, I. Matsuo and S. Yamada, Chem. Pharm. Bull., 1965, 13, 995.
12. A. Ito, R. Takahashi and Y. Baba, Chem. Pharm. Bull., 1975, 23, 3081.
13. H. C. Brown and B. C. Subba Rao, J. Am. Chem. Soc., 1960, 82, 681.
14. A. S. B. Prasad, J. V. B. Kanth and M. Periaswamy, Tetrahedron, 1992, 48, 4623.
15. M. J. McKennon and A. I. Meyers, J. Org. Chem., 1993, 58, 3568.
16. G. Kokotos and C. Noula, J. Org. Chem., 1996, 61, 6994.
17. J. Kovacs, R. Giannotti and A. Kapoor, J. Am. Chem. Soc., 1966, 88, 2282.