Diastereoselective solid-phase radical addition to oxime ether anchored to polymer support

Chemical and Pharmaceutical Bulletin

Volumn 51, Issue 5, 2003, Pages 540-544

  Miyabe, Hideto ^a,b   Konishi, Chihiro ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Diastereoselective; Oxime ether; Radical reaction; Solid phase

Indexed keywords

AMINO ACID DERIVATIVE; BORANE DERIVATIVE; ETHER DERIVATIVE; OXIME DERIVATIVE; POLYMER; ZINC DERIVATIVE; AMINO ACID; DIETHYLZINC; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ORGANOMETALLIC COMPOUND; OXIME; TRIETHYLBORANE;

ADDITION REACTION; ARTICLE; DIASTEREOISOMER; LOW TEMPERATURE; SOLID; SYNTHESIS; CHEMISTRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; TEMPERATURE; THIN LAYER CHROMATOGRAPHY;

AMINO ACIDS; BORANES; CHROMATOGRAPHY, THIN LAYER; ETHERS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLIC COMPOUNDS; OXIMES; POLYMERS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM; TEMPERATURE;

EID: 0642371240     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.51.540     Document Type: Article

References (30)

1. Brown R. C. D., J. Chem. Soc., Perkin Trans. 1, 1998, 3293-3320 (1998).
2. Chem. Rev., 97 (1997), whole issue of No. 2, pp. 347-510.
3. Hermkens P. H. H., Ottenheijm H. C. J., Rees D. C., Tetrahedron, 53, 5643-5678 (1997).
4. Balkenhohl F., von dem Bussche-Hünnefeld C., Lansky A., Zechel C., Angew. Chem., Int. Ed. Engl., 35, 2288-2337 (1996).
5. Früchtel J. S., Jung G., Angew. Chem., Int. Ed. Engl., 35, 17-42 (1996).
6. Thompson L. A., Ellman J. A., Chem. Rev., 96, 555-600 (1996).
7. Acc. Chem. Res., 29 (1996), whole issue of No. 3, pp. 112-170.
8. Hermkens P. H. H., Ottenheijm H. C. J., Rees D., Tetrahedron, 52, 4527-4554 (1996).
9. Routledge A., Abell C., Balasubramanian S., Synlett, 1997, 61-62 (1997).
10. Du X., Armstrong R. W., J. Org. Chem., 62, 5678-5679 (1997).
11. Du X., Armstrong R. W., Tetrahedron Lett., 39, 2281-2284 (1998).
12. Berteina S., De Mesmaeker A., Tetrahedron Lett., 39, 5759-5762 (1998).
13. Berteina S., Wendeborn S., De Mesmaeker A., Synlett, 1998, 1231-1233 (1998).
14. Watanabe Y., Ishikawa S., Takao G., Toru T., Tetrahedron Lett., 40, 4535-4538 (1999).
15. Caddick S., Hamza D., Wadman S. N., Tetrahedron Lett., 40, 7285-7288 (1999).
16. Zhu X., Ganesan A., J. Comb. Chem., 1, 157-162 (1999).
17. Enholm E. J., Gallagher M. E., Jiang S., Batson W. A., Org. Lett., 2, 3355-3357 (2000).
18. Sibi M. P., Chandramouli S. V., Tetrahedron Lett., 38, 8929-8932 (1997).
19. Miyabe H., Fujishima Y., Naito T., J. Org. Chem., 64, 2174-2175 (1999).
20. Miyabe H., Tanaka H., Naito T., Tetrahedron Lett., 40, 8387-8390 (1999).
21. Miyabe H., Fujii K., Tanaka H., Naito T., Chem. Commun., 2001, 831-832 (2001).
22. Miyabe H., Konishi C., Naito T., Org. Lett., 2, 1443-1445 (2000).
23. Miyabe H., Ushiro C., Naito T., Chem. Commun., 1997, 1789-1790 (1997).
24. Miyabe H., Ushiro C., Ueda M., Yamakawa K., Naito T., J. Org. Chem., 65, 176-185 (2000).
25. Diether R. K., Datar R., Can. J. Chem., 71, 814-823 (1993).
26. Moody C. J., Gallagher P. T., Lightfoot A. P., Slawin A. M. Z., J. Org. Chem., 64, 4419-4425 (1999).
27. Wang resins purchased from Novabiochem was used in all experiments.
28. Miyabe H., Ueda M., Yoshioka N., Naito T., Synlett, 1999, 465-467 (1999).
29. Miyabe H., Fujii K., Naito T., Org. Lett., 1, 569-572 (1999).
30. Ryu I., Araki F., Minakata S., Komatsu M., Tetrahedron Lett., 39, 6335-6336 (1998).