Remote asymmtric induction: Synthesis of C-linked α-galactoserine and homoserine derivatives by electrophilic amination

Tetrahedron Letters

Volumn 39, Issue 34, 1998, Pages 6131-6134

  Arya, Prabhat ^a   Ben, Robert N ^a   Qin, Huiping ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA GALACTOSERINE; GLYCOPEPTIDE; HOMOSERINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; BINDING SITE; CHIRALITY; ELECTRIC CONDUCTIVITY; PEPTIDE ANALYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032552170     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01295-7     Document Type: Article

References (20)

1. 1. NRCC publication no. 40877.
2. 2. (a) Kihlberg, J.; Elofsson, M. Curr. Med. Chem. 1997, 4, 85 and references therein,
3. (b) Sears, P.; Wong, C.-H. Proc. Natl. Acad. Sci. USA 1996, 93, 12086.
4. (v) Dwek, R. A. Chem. Rev. 1996, 96, 683.
5. (d) Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321.
6. (e) Varki, A. Glycobiology 1993, 3, 97.
7. (f) Sharon, N.; Lis, H. Sci. Am. 1993 (January), 82.
8. (g) Bill, R. M.; Flitsch, S. Chem. Biol. 1996, 3, 145.
9. 3. (a) Rodriguez, E. C.; Winans, K. A.; King, D. S.; Bertozzi, C. R. J. Am. Chem. Soc. 1997, 119, 9905 and references therein,
10. (b) Sames, D.; Chen, X.-T. Danishefsky, S. J. Nature, 1997, 389, 587.
11. (c) Seitz, O.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8766.
12. 4. (a) Ben, R. N.; Orellana, O.; Arya, P. J. Org. Chem. 1998 (in press).
13. (b) Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897.
14. (c) Bertozzi, C. R.; Hoeprich, Jr., P. D.; Bednarski, M. D. J. Org. Chem. 1992, 57. 6092.
15. (d) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzalez-Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639.
16. (e) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem. Int. Ed. Engl. 1992, 31, 902.
17. (f) Gurjar, M. K.; Mainker, A. S.; Syamala, M. Tetrahedron: Asymmetry 1993, 4, 2343.
18. (g) Frey, O.; Hoffmann, M.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2026.
19. (h) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1997, 36, 1191.
20. +