Synthesis of 9-fluorenylmethoxycarbonyl-protected amino aldehydes

Tetrahedron Asymmetry

Volumn 9, Issue 11, 1998, Pages 1855-1858

  Wen, James J ^a   Crews, Craig M ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; AMINOALDEHYDE;

ALCOHOL OXIDATION; ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; REDUCTION; SYNTHESIS;

EID: 0032486152     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00183-9     Document Type: Article

References (17)

1. 1. (i) Billich, S.; Knoop, M. T.; Hansen, J.; Sedlacek, J.; Mertz, R.; Moelling, K. J. Biol. Chem. 1988, 263, 17905-17908.
2. (ii) Martinez, J.; Bali, J. P.; Rodriguez, M.; Castro, B.; Magous, R.; Laur, J.; Lignon, M. F. J. Med. Chem. 1985, 28, 1874-1879.
3. 2. (i) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides and Proteins (B. Weinstein, ed.), Marcel Dekker, New York, 1983, VII, pp. 267-357.
4. (ii) Ma, S. G.; Spatola, A. F. Int. J. Peptide Protein Res. 1993, 41, 204-206.
5. 3. Sasaki, Y.; Coy, D. H. Peptides 1987, 8, 119-121.
6. 4. Wang, S. S. J. Amer. Chem. Soc. 1973, 95, 1328-1333.
7. 5. Rink, H. Tetrahedron Lett. 1987, 28, 3787-3790.
8. 6. Brown, H. C.; Heim, P.; Yoon, N. M. J. Amer. Chem. Soc. 1970, 92, 1637-1646.
9. +] 179.2, found 179.1.
10. 8. Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; Martinez, J. Tetrahedron Lett. 1991, 32, 923-926.
11. 9. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 31, 2647-2650.
12. 10. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1979, 5, 399-402.
13. 11. Parikh, J. R.; Doering, W. von E. J. Amer. Chem. Soc. 1967, 89, 5505-5507.
14. 12. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
15. 13. The yield of the Swern oxidation for Fmoc-Met-ol was low (25%), possibly resulting from the involvement of the thioether side chain of Fmoc-Met-ol during the oxidation. Mechanistic studies of the Swern oxidation on other thioether containing compounds are currently in progress and will be reported in due course.
16. 14. Fehrentz, J. A.; Castro, B. Synthesis 1983, 676-678.
17. 15. Pizey, J. S. Synthetic Reagents, Vol. 1, Wiley, New York, 1974; pp. 101-294.