Efficient Mitsunobu reactions with N-phenylfluorenyl or N-trityl serine esters

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2544-2546

  Cherney, Robert J ^a   Wang, Li ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SERINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029866699     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951958t     Document Type: Article

References (17)

1. (a) Mitsunobu, O. Synthesis 1981, 1.
2. (b) Hughes, D. L. Org. React. 1992, 42, 335.
3. Wojciechowska, H.; Pawlowicz, R.; Andruszkiewicz, R.; Grzybowska, J. Tetrahedron Lett. 1978, 4063.
4. Arnold, L. D., Kalantar, T. H ; Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105.
5. Miller, M. J. Acc. Chem. Res 1986, 19, 49.
6. Galeotti, N.; Montagne, C.; Poncet, J ; Jouin, P. Tetrahedron Lett. 1992, 2807. Wipf, P.; Miller, C. P Tetrahedron Lett. 1992, 6267.
7. Galeotti, N.; Montagne, C.; Poncet, J ; Jouin, P. Tetrahedron Lett. 1992, 2807. Wipf, P.; Miller, C. P Tetrahedron Lett. 1992, 6267.
8. Nagai, U.; Kato, R.; Pavone, V. Peptide Chem. 1987, 187.
9. (a) Golding, B. T.; Howes, C. J. Chem. Res. (S) 1984, 1.
10. (b) Otsuka, M., Kittaka, A.; Iimori, T.; Yamashita, H., Kobayashi, S.; Ohno, M. Chem. Pharm. Bull. 1985, 33, 509.
11. (c) Fabiano, E.; Golding, B. T.; Sadeghi, M. M. Synthesis 1987, 190.
12. Martin, S. F ; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017.
13. Christie, B. D.; Rapoport, H. J. Org. Chem. 1985, 50, 1239.
14. Guthrie, R. D.; Nicolas, E. C J Am Chem Soc. 1981, 103, 4638.
15. Baldwin, J. E.; Spivey, A. C., Schofield, C. J.; Sweeney, J. B. Tetrahedron 1993, 49, 6309.
16. 2 to remove the N-phenylfluorenyl or N-trityl protecting group. The solution was concentrated and reacted with the (R)-Mosher acid chloride (Fluka) to give the corresponding amide: Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
17. Lubell, W.; Rapoport, H. J. Org Chem. 1989, 54, 3824.