Aspects of the Algar-Flynn-Oyamada (AFO) reaction

Tetrahedron

Volumn 52, Issue 20, 1996, Pages 7163-7178

  Bennett, Michael ^a   Burke, Anthony J ^a,b   O'Sullivan, W Ivo ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHALCONE DERIVATIVE; FLAVONOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029931889     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00334-1     Document Type: Article

References (26)

1. (a) Algar, J.; Flynn, J.P. Proc. R. Ir. Acad. 1934, 42B, 1;
2. (b) Oyamada, T., J. Chem. Soc. Japan 1934, 55, 1256 and Bull. Chem. Soc. Japan 1935, 10, 182.
3. (b) Oyamada, T., J. Chem. Soc. Japan 1934, 55, 1256 and Bull. Chem. Soc. Japan 1935, 10, 182.
4. Cummins, B.; Donnelly, D.M.X.; Eades, J.F.; Fletcher, H.; O'Cinnéide, F.; Philibin, E.M.; Swirski, J.; Wheeler, T.S.; Wilson, R.K. Tetrahedron 1963, 19, 499.
5. Geissman, T.A.; Fukushima, D.K. J. Am. Chem. Soc. 1948, 70, 1686.
6. Dean, F.M.; Podimuang, V. J. Chem. Soc., 1965, 3978.
7. Brady, B.A.; O'Sullivan, W.I.; Philibin, E.M. J. Chem. Soc. Chem. Commun. 1970, 1435.
8. (a) Donnelly, D.M.X.; Lavin, T.P.; Melody, D.P.; Philbin, E.M. J. Chem. Soc. Chem. Commun. 1965, 460;
9. (b) Cullen, W.P.; Donnelly, D.M.X.; Keenan, A.K.; Lavin, T.P.; Melody, D.P.; Philibin, E.M. J. Chem. Soc. (C) 1971, 2848.
10. The prefix erythro is used to denote the αR, βS stereochemistry, whilst the prefix threo will be used to denote the αR, βR stereochemistry.
11. Brady, B.A.; Geoghegan, M.; O'Sullivan, W.I. J. Chem. Soc., Perkin Trans. 1 1989, 1557.
12. Buchanan, J.G.; Sable, H.Z. in Selective Organic Transformations, Thyagarajan, B.S. Ed., Wiley-Interscience: New York, 1972; vol. 2, and references cited therein.
13. Zimmerman, H.E.; Ahramjian, L. J. Am. Chem. Soc. 1959, 81, 2086.
14. Fischer, F.; Arlt, W. Chem. Ber. 1964, 97, 1910.
15. Volsteedt, F. du R.; Rall, G.J. H.; Roux, D.G. Tetrahedron lett. 1973, 12, 1001.
16. 1H nmr spectrum, even though the later cross-over aldol reaction using benzofuranone 7 as substrate would suggest its existence.
17. Gormley, T.R.; O'Sullivan, W.I. Tetrahedron, 1973, 29, 369.
18. Adams, C.J.; Main, L. Tetrahedron, 1991, 47, 4959.
19. Baldwin, J.E. J. Chem. Soc. Chem. Commun. 1976, 734.
20. These benzofuranone isomers were previously used to tentatively assign the stereochemistry of the solvolysis products of some aurone epoxides (see ref. 9).
21. Kimura, Y.; Hoshi, M. Proc. Imp. Acad. Japan 1936, 12, 285.
22. Freudenberg, K. Fikentscher, H.; Harder, M. Annalen, 1925, 441, 157.
23. Varma, M.; Varma, R.S.; Parthasarathy, M.R. J. Prakt. Chem., 1983, 325, 382.
24. As this d.e. value was based upon the isolated yields of the erythro and threo isomers it is reasonable to assume that the d.e. was much higher, and reason to suggest this comes from the fact that when a similar aldol reaction was conducted upon 2, 6-dimethoxybenzo[b]furan-3(2H)-one and benzaldehyde a d.e. of 62% was obtained for erythro-2,6-dimethoxy-2-(hydroxyphenylmethyl)benzo[b]furan-3(2H)-one (These results will be reported in a later publication by us).
25. Row, L.R.; Seshadri, T.R. Proc. Indian Acad. Sci. 1964, 23A, 26.
26. (a) On the basis of the analytical data given, it could also possibly be the isomeric benzoquinone 22b; (b) On the basis of the analytical data given, it could also possibly be the isomeric benzoquinone 23b.