Synthesis of enantiomerically pure quaternary glutamic acids via chemo- and diastereoselective alkylation of (5S)-3-([2-methoxycarbonyl]ethyl)-5-phenyl-5, 6-dihydro-2H,4-oxazin-2-one

Arkivoc

Volumn 2000, Issue 5 SPEC.ISS., 2000, Pages 820-831

  Harwood, Laurence M ^a   Tyler, Simon N G ^a   Drew, Michael G B ^a   Jahans, Archie ^a   MacGilp, Iain D ^b  

^a UNIVERSITY OF READING   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACID; OXAZINE DERIVATIVE;

ADDITION REACTION; ALKYLATION; ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; ENANTIOMER; GRIGNARD REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 13544264697     PISSN: 14246376     EISSN: 14246376     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. S. N. G. Tyler, L. M. Harwood and I. D. MacGilp, Abstracts of Papers of the American Chemical Society, 1998, 216, 201-ORGN.
2. L. M. Harwood, K. J. Vines and M. G. B. Drew, Synlett, 1996, 1051.
3. D. Ager, N. Cooper, G. G. Cox, F. Garro-Hélion, and L. M. Harwood, Tetrahedron: Asymmetry, 1996, 7, 2563.
4. C. M. Shafer and T. F. Molinski, J. Org. Chem., 1996, 61, 2044.
5. L. M. Harwood, S. N. G. Tyler, A. S. Anslow, I. D. MacGilp and M. G. B. Drew, Tetrahedron: Asymmetry, 1997, 8, 4007.
6. M. J. Neal, Medical Pharmacology at a Glance, Second Edition, Blackwell Science, Oxford, 1992, p. 48.
7. J. Dyer, S. Keeling and M. G. Moloney, Chem. Commun., 1998, 461 and references cited therein; S. G. Pyne, K. Schafer, B. W. Skelton and A. H. White, Chem. Commun., 1997, 2267 and references cited therein.
8. J. Dyer, S. Keeling and M. G. Moloney, Chem. Commun., 1998, 461 and references cited therein; S. G. Pyne, K. Schafer, B. W. Skelton and A. H. White, Chem. Commun., 1997, 2267 and references cited therein.
9. All novel compounds isolated gave spectroscopic data and combustion analyses or high resolution mass spectrometric data in accordance with their assigned structures.
10. G. G. Cox and L. M. Harwood, Tetrahedron: Asymmetry, 1994, 5, 1669.
11. Y. Sugita, Agric. Biol. Chem., 1989, 53, 129.
12. The Merck Index, Twelfth Edition, ed. S. Budavari, Merck and Company, Rahway, 1996.
13. J. G. Salway, Metabolism at a Glance, Blackwell Science, Oxford, 1994, p. 42.
14. a radiation. Data analysis for both structures was carried out with the XDS program.15 The structures were determined by direct methods using SHELXS616 and refined (non-heavy atoms anisotropic, hydrogen atoms in calculated positions, isotropic) by full-matrix least squares17 on F2 using SHELXL to R 0.0742 for 5a and R 0.0545 for 5c. Atomic co-ordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre. See Instructions to Authors, Issue No. 1, 1999.
15. th Edn., ed S. Budavari, Merck & Co., Rahway, 1996.
16. W. Kabsch, J. Appl. Cryst., 1988, 21, 916.
17. G. M. Sheldrick, SHELX86, Acta Cryst., 1990, A46, 467.
18. G. M. Sheldrick, SHELXL93, a program for crystal structure refinement, University of Göttingen, 1993.
19. M. J. Neal, Medical Pharmacology at a Glance, Second Edition, Blackwell Science, Oxford, 1992, p. 48.
20. J. Dyer, S. Keeling and M. G. Moloney, Chem. Commun., 1998, 461 and references cited therein; S. G. Pyne, K. Schafer, B. W. Skelton and A. H. White, Chem. Commun., 1997, 2267 and references cited therein.
21. J. Dyer, S. Keeling and M. G. Moloney, Chem. Commun., 1998, 461 and references cited therein; S. G. Pyne, K. Schafer, B. W. Skelton and A. H. White, Chem. Commun., 1997, 2267 and references cited therein.