A convenient procedure for the reduction of S-(+)-silyl serine methyl ester to chiral serinol derivatives

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1743-1746

  Novachek, Katherine A ^a   Meyers, A I ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SERINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS;

EID: 0029921898     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00164-5     Document Type: Article

References (28)

1. (a) Asymmetric Synthesis, Coppola, G. M., Schuster, H. F. John Wiley and Sons, New York, 1987.
2. (b) Loai, K.; Niwa, B. Chem. Rev., 1992, 92, 833.
3. (c) Blaser, H.-U. Chem. Rev., 1992, 92, 935.
4. (d) Evans, D. A., Asymmetric Synthesis, ed. J. D. Morrison, Academic, New York, Vol. 3.
5. (e) Tomioka, K. Synthesis, 1990, 541.
6. (a) Prasad, B.; Saund, A. K.; Bora, J. M.; Mathur, N. K. Indian J. Chem. 1974, 12, 290.
7. (b) Lane, C. F., U.S. Patent 3 935 280, Jan 27, 1976, Chem Abstr. 1976, 84, 135101p.
8. (c) Smith, G. A.; Gawley, R. E. Org. Synth. 1985, 63, 136.
9. (d) Gage, J. R.; Evans, D. A. Org. Synth. 1989, 68, 77.
10. (e) Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. Organic Syntheses, Wiley, New York, 1990; Collect Vol. VII, p 530.
11. (f) Giannis, A.; Sandhoff, K. Angew. Chem. Int. Ed. Eng. 1989, 28, 218.
12. (g) Dharanipragada, R.; Alarcon, A.; Hruby, V. J. Org. Prep. Proc. Int. 1991, 23, 396.
13. (h) Boesten, W. H. J.; Schepers, C. H. M.; Roberts, M. J. A. Eur Pat. Appl. EPO 322 982 A2, July 5, 1989, Chem. Abstr. 1989, 111, 233669a.
14. (i) Abiko, A.; Masamune, S. Tetrahedron Lett. 1992, 33, 5517.
15. (j) McKennon, M. J.; Meyers, A. I.; Drauz, K.; Schwarm, M. J. Org. Chem. 1993, 58, 3568.
16. For examples see ref 1a., also Gonda, J.; Helland, A. C.; Ernst, B.; Bellus, D. Synthesis, 1993, 729. Sibi, M. P.; Rutherford, D.; Sharma, R. J. Chem. Soc. Perk. Trans. 1, 1994, 1675.
17. For examples see ref 1a., also Gonda, J.; Helland, A. C.; Ernst, B.; Bellus, D. Synthesis, 1993, 729. Sibi, M. P.; Rutherford, D.; Sharma, R. J. Chem. Soc. Perk. Trans. 1, 1994, 1675.
18. Meyers, A. I.; Schmidt, W.; McKennon, M. J. Synthesis, 1993, 250.
19. -1, 254 nm
20. von M. Brenner, Huber, W. Helv. Chim. Acta. 1953, 36, 1109.
21. 3) -6.2, -5.8, 17.93, 25.48, 51.64, 55.26, 65.16, 174.24.
22. 5 of the hydroxymethyl oxazoline 5, to be 93-95%.
23. Tkaczuk, P.; Thorton, E. R. J. Org. Chem. 1981, 46, 4393.
24. Dale, J. A.; Mosher, H. S. J. Amer. Chem. Soc. 1973, 35, 512.
25. HPLC analysis immediately following reduction gave a ratio of 96:4. After 2 weeks under the described storage conditions, a ratio of 94:6 was observed following formation of the oxazoline.
26. Greene, T. Protective Groups in Organic Synthesis. Wiley Interscience, 1981.
27. For conjugate addition to nonchelating 1-naphthyl oxazolines see Rawson, D. J.; Meyers, A. I. J. Org. Chem. 1991, 56, 2607. For additions to α,β-unsaturated acyclic nonchelating oxazolines see Shipman, M.; Meyers, A. I. J. Org. Chem. 1991, 56, 7098.
28. For conjugate addition to nonchelating 1-naphthyl oxazolines see Rawson, D. J.; Meyers, A. I. J. Org. Chem. 1991, 56, 2607. For additions to α,β-unsaturated acyclic nonchelating oxazolines see Shipman, M.; Meyers, A. I. J. Org. Chem. 1991, 56, 7098.