Novel chiral templates for 1,3-oxazolium-4-olate (isomunchnone) cycloadditions: (5R)- and (5S)-phenyloxazin-2,3-dione

Tetrahedron Letters

Volumn 38, Issue 17, 1997, Pages 3107-3110

  Angell, Richard ^c   Drew, Michael G B ^a   Fengler Veith, Marion ^a   Finch, Harry ^c   Harwood, Laurence M ^a   Jahans, Archie W ^a   Tucker, Toby T ^b  

^a UNIVERSITY OF READING   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 OXAZINE DERIVATIVE; OXAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; CRYSTALLOGRAPHY; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030994013     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00557-1     Document Type: Article

References (25)

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19. The preparation and use of succinimidyl diazoacetate was first reported by : Quihia, L.; Renê, L.; Guilhem, J.; Pascard, C.; Badet, B. J. Org. Chem. 1993, 58, 1641. We followed a modified method by: Doyle, M. P.; Kalinin, A. V. J. Org. Chem. 1996, 61, 2179.
20. The preparation and use of succinimidyl diazoacetate was first reported by : Quihia, L.; Renê, L.; Guilhem, J.; Pascard, C.; Badet, B. J. Org. Chem. 1993, 58, 1641. We followed a modified method by: Doyle, M. P.; Kalinin, A. V. J. Org. Chem. 1996, 61, 2179.
21. 2)H), 6.01 (1H, bs, 5-H), 4.89 (1H, dd, J 12.1, J 2.8 Hz, 6α-H), 4.73 (1H, dd, J 12.1,J 2.0 Hz, 6β-H).
22. -3, F(000) = 840.3197 independent reflections [R(int) = 0,016] were collected on a Marresearch Image Plate. The structure was solved by direct methods and refined by full-matrix least squares (non-hydrogen atoms anisotropic and hydrogen atoms isotropic in calculated positions) to an R of 0.0325 for 2955 data with I>2σ(I). Crystal Data for all structures have been deposited at the Cambridge Crystallographic Data Centre.
23. Dellaria, J., F.; Santarsiero, B. D. J. Org. Chem. 1989, 54, 3916.
24. All novel compounds described had structures in accordance with their spectroscopic data.
25. 1H-NMR of the crude material the cycloadducts 7 and 8 were obtained in a ratio of 53 : 47; the isomers 9 and 10 in a ratio of 76 : 24.