Highly Stereoselective Conversion of Aryl Peptidyl Ketones into the Corresponding Peptide Alcohols

European Journal of Organic Chemistry

Volumn , Issue 3, 2004, Pages 463-467

  Di Gioia, Maria Luisa ^a   Leggio, Antonella ^a   Le Pera, Adolfo ^a   Liguori, Angelo ^a   Siciliano, Carlo ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

Alcohols; Peptides; Reduction; Stereoselectivity; Titanium

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; AMINO ACID; CYANIDE; HYDROGEN; KETONE; PEPTIDE; TITANIUM TETRACHLORIDE; URETHAN;

AMINO TERMINAL SEQUENCE; ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; METHODOLOGY; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 1242263437     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300563     Document Type: Article

References (16)

1. D. J. Ager, I. Prakash, D. R. Schood, Chem. Rev. 1996, 96, 835-856.
2. M. R. Paleo, I. Cabeza, F. J. Sardina, J. Org. Chem. 2000, 65, 2108-2113.
3. J. Pless, W. Banei, F. Cardinaux, A. Closse, D. Hauser, R. Huguenia, D. Roemer, R. C. Hill, Helv. Chem. Acta 1979, 62, 398-401.
4. T. Kunieda, T. Ishizuka, Stud. Nat. Prod. Chem. 1993, 12, 411-417.
5. J. Engel, Chem.-Ztg. 1982, 106, 169-172.
6. C. Auvin-Guette, S. Rebuffant, Y. Prigent, B. Bodo, J. Am. Chem. Soc. 1992, 114, 2170-2174.
7. R. C. Pandey, J. C. Cook Jr., K. L. Rinehart Jr., J. Am. Chem. Soc. 1977, 99, 5205-5206.
8. K. L. Rinehart Jr., L. A. Gaudosio, M. L. Moore, R. C. Pandey, J. C. Cook Jr., M. Barber, R. D. Sedgwick, R. S. Bordoli, A. N. Tyler, B. N. Green, J. Am. Chem. Soc. 1981, 103, 6517-6520.
9. K.M. Das, S. Raghothama, P. Balaram, Biochemistry 1986, 25, 7110-7117.
10. R. Thompson, Methods Enzymol. 1977, 46, 220-225.
11. R. P. Sharma, M. G. Gore, M. Akhton, J. Chem. Soc. Chem. Commun. 1979, 875-877.
12. C. F. Stanfeld, J. E. Parker, P. Kanellis, J. Org. Chem. 1981, 46, 4797-4798.
13. M. Nishikata, H. Yokosawa, S. I. Ishii, Chem. Pharm. Bull. 1986, 34, 2931-2936.
14. K. Soai, H. Oyamada, M. Takase, Bull. Chem. Soc. Jpn. 1984, 57, 2327-2328.
15. G. Kokotos, Synthesis 1990, 299-301.
16. M. L. Di Gioia, A. Leggio, A. Liguori, A. Napoli, C. Siciliano, G. Sindona, J. Org. Chem. 2001, 66, 7002-7007.