Cycloadditions of 1,3-oxazolium-4-olates (Isomunchnones) by Rhodium(II)-Induced decomposition of α-Diazocarbonyl derivatives of (5R)- and (5S)-phenyloxazin-3-one as a chiral template

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4517-4520

  Angell, Richard ^c   Fengler Veith, Marion ^a   Finch, Harry ^c   Harwood, Laurence M ^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

DIAZONIUM COMPOUND; RHODIUM COMPLEX;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DECOMPOSITION; DIASTEREOISOMER; DRUG SYNTHESIS; ISOMER;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0030948942     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00918-0     Document Type: Article

References (18)

1. See previous publication: Angell, R.; Drew, M. G. B.; Fengler-Veith, M.; Finch, H.; Harwood, L. M.; Jahans, A. W.; Tucker, T. T. Tetrahedron Lett. 1997 (in press).
2. Clark, F. J. Org. Chem. 1962, 3251.
3. Padwa, A.; Hertzog, D. L. Tetrahedron 1993, 49, 2589.
4. Sato, M.; Kanuma, N.; Kato, T. Bull Chem. Soc. Jpn. 1982, 30, 1315.
5. Regitz, M.; Hocker, J.; Leidhegger, A. "Organic Synthesis", John Wiley, New York, 1973, 179.
6. 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.
7. 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.
8. a) Padwa, A.; Austin, D. J.; Price, A. T.; Weingarten, M. D. Tetrahedron 1996, 52, 3247.
9. b) Padwa, A.; Prein, M. Tetrahedron Lett. 1996, 37, 6981.
10. c) Padwa, A.; Sandanayaka, V. P.; Curtis, F.A. J. Am. Chem. Soc. 1994, 116, 2667.
11. d) Padwa, A.; Dean, D. C. ; Fairfax, D. J.; Xu, S. L. J. Org. Chem. 1993, 58, 4646.
12. e) Cox, C. G.; Moody, C. J.; Austin, D. J.; Padwa, A. Tetrahedron 1993, 49, 5109.
13. f) Padwa, A.; Chinn, R. L.; Hornbuckle, S. F.; Zhang, Z. J. J. Org. Chem. 1991, 56, 3271.
14. g) Doyle, M. P.; Bagheri, V.; Wandless, T. J.; Harn, N. K.; Brinker, D. A.; Eagle, C. T.; Loh, K. J. Am. Chem. Soc. 1990, 112, 1960.
15. h) Demonceau, A.; Noels, A. F.; Hubert, A. J. Tetrahedron 1990, 46, 3889.
16. i) Doyle, M. P. Chem. Rev. 1986, 86, 919. References cited therein.
17. 3).
18. Illustrative NOE results for cycloadduct 6b.