A New Route to Functionalised Oxazoles

Synlett

Volumn 1996, Issue 9, 1996, Pages 825-826

  Bagley, Mark C ^a   Buck, Richard T ^a   Hind, S Lucy ^a   Moody, Christopher J ^a   Slawin, Alexandra M Z ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002910160     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5607     Document Type: Article

References (22)

1. Pattenden, G. J. Heterocyclic Chem. 1992, 29, 607-618.
2. Michael, J. P.; Pattenden, G. Angew. Chem. 1993, 105, 1; Angew. Chem., Int. Ed. Engl. 1993, 32, 1.
3. Michael, J. P.; Pattenden, G. Angew. Chem. 1993, 105, 1; Angew. Chem., Int. Ed. Engl. 1993, 32, 1.
4. Wipf, P. Chem. Rev. 1995, 95, 2115-2134.
5. Cf. Li, G.; Warner, P. M.; Jebaratnam, D. J. J. Org. Chem. 1996, 61, 778-780.
6. Doyle, K. J.; Moody, C. J. Tetrahedron 1994, 50, 3761-3772.
7. Doyle, K. J.; Moody, C. J. Synthesis 1994, 1021-1022.
8. Padwa, A.; Austin, D. J. Angew. Chem. 1994, 106, 1881; Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
9. Padwa, A.; Austin, D. J. Angew. Chem. 1994, 106, 1881; Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
10. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160.
11. Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811-10843.
12. For the early work, see: Cama, L. D.; Christensen, B. G. Tetrahedron Lett. 1978, 44, 4233-4236.
13. For recent examples, see ref. 12 and: Mastalerz, H.; Menard, M. J. Org. Chem. 1994, 59, 3223-3226.
14. Bouthillier, G.; Mastalerz, H.; Menard, M. Tetrahedron Lett. 1994, 35, 4689-4692.
15. For recent examples, see refs. 14 and 15 and: Haigh, D. Tetrahedron 1994, 50, 3177-3194.
16. Ferris, L.; Haigh, D.; Moody, C. J. Synlett 1995, 921-922.
17. Landais, Y.; Planchenault, D. Synlett 1995, 1191-1193.
18. Typical procedure: A solution of the diazoketoester (1.0 g, 7.0 mmol, 1.4 equiv.) in dry chloroform (35 ml) was added dropwise over 6 h to a refluxing solution of the amide (5.0 mmol, 1.0 equiv) and rhodium(II) acetate (44 mg, 0.10 mmol, 0.02 equiv.) in dry chloroform (130 ml). The mixture was refluxed for a further 30 min, allowed to cool, evaporated in vacuo and purified by flash chromatography on silica, eluting with ethyl acetate-light petroleum (1 : 1).
19. The rhodium catalysed N-H insertion reaction of methyl 3,3,3-trifluoro-2-diazopropionate with Cbz-phenylalaninamide has been reported very recently: Osipov, S. N.; Sewald, N.; Kolomiets, A. F.; Fokin, A. V.; Burger, K. Tetrahedron Lett. 1996, 37, 615-618.
20. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604-3606.
21. 2).
22. The crystallographic data have been deposited at the Cambridge Crystallographic Data Centre.