A practical synthesis of enantiopure (S)-4-(4-hydroxybenzyl)-oxazolidin-2-one

Tetrahedron Asymmetry

Volumn 14, Issue 17, 2003, Pages 2619-2623

  Green, Rachel ^a   Taylor, Piers J M ^a   Bull, Steven D ^a   James, Tony D ^a   Mahon, Mary F ^a   Merritt, Andy T ^b  

^a University of Bath Claverton Down   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 (4 BENZYLOXYBENZYL)OXAZOLIDIN 2 ONE; 4 (4 HYDROXYBENZYL)OXAZOLIDIN 2 ONE; BENZYL DERIVATIVE; N TERT BUTYLOXYCARBONYLTYROSINE; O BENZYL N TERT BUTYLOXYCARBONYLTYROSINE BENZYL ESTER [3 (4 BENZYLOXYPHENYL) 2 TERT BUTYLOXYCARBONYLAMINOPROPIONIC ACID BENZYL ESTER]; O BENZYL N TERT BUTYLOXYCARBONYLTYROSINOL [1 (4 BENZYLOXYBENZYL) 2 HYDROXYETHYL]CARBAMIC ACID TERT BUTYL ESTER; OXAZOLIDINE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; POLYMER; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CRYSTAL STRUCTURE; PRIORITY JOURNAL; SYNTHESIS;

EID: 0041830946     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00482-8     Document Type: Article

References (22)

1. Obrecht D., Villalgordo J.M. Solid-Supported Combinatorial and Parallel Synthesis of Small Molecular-Weight Compound Libraries. 17:1998;Tetrahedron Organic Chemistry Series, Oxford.
2. Kirchoff J.H., Lormann M.E., Brase S. Chim. Oggi. 19:2001;8.
3. Burgess K., Lim D.J. Chem. Commun. 1997;785.
4. Purandare A.V., Natarajan S. Tetrahedron Lett. 38:1997;8777.
5. Phoon C.W., Abell C. Tetrahedron Lett. 39:1998;2655.
6. Winkler J.D., McCoull W. Tetrahedron Lett. 39:1998;4935.
7. Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265.
8. Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron. 57:2001;8313.
9. For an alternative approach where a polymer supported oxazolidin-2-one derived from L-tyrosine was constructed 'on bead' from polymer supported L-tyrosinol see Ref. 4.
10. Sudharshan M., Hultin P.G. Synlett. 1997;171.
11. Gage J.R., Evans D.A. Org. Synth. 68:1990;78.
12. L-N-Boc-Tyrosine is commercially available from Aldrich, or may be prepared from L-tyrosine in 92% yield according to the method of: Jung M., Lazarove T. J. Org. Chem. 62:1997;1553.
13. Chen C., Zhu Y., Wilcoxen K. J. Org. Chem. 65:2000;2574.
14. Dondoni A., Perrone D., Semola T. Synthesis. 1995;181.
15. Hanessian S., Ninkovic S. J. Org. Chem. 16:1996;5418.
16. Bach T., Schlummer B., Harms K. Chem. Commun. 2000;287.
17. The CDS system program Conquest (Version 1.4) was used.
18. Allen F.H., Kennard O. Chem. Des. Autom. News. 8:1993;1.
19. Allen F.H., Kennard O. Chem. Des. Autom. News. 8:1993;31.
20. Crystallographic data (excluding structure factors) for the structure in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 209597.
21. Nakata T., Nakatani M., Masaru T., Okai J., Kawoaka Y. Bull. Chem. Soc. Jpn. 69:1996;1099.
22. Spaltenstein A., Carpino P.A., Miyake F., Hopkins P.B. J. Org. Chem. 17:1987;3759.