By Michael Harmata
This quantity offers paintings from six various teams engaged on a variety of facets of cycloaddition chemistry. Jos? Mascare?as offers us a truly fascinating account of the chemistry of &Bgr;-alkoxy-&ggr;-pyrones and comparable species. Al Padwa and Chris Staub speak about additional advances in rhodium carbenoid chemistry and the weird cycloaddition techniques attainable with those intermediates. larger order cycloadditions mediated through transition metals spotlight Jim Rigby's replace on his group's efforts during this quarter. Lily Lee and John Snyder current us with a close account of the indole ring as a dienophile, tough us to think about the untapped power during this sector. Brian Keay and Ian Hunt talk about the intramolecular Diels-Alder reactions of furan; a document that's either top-notch technology, and what can be a nice studying device for college students who have to see how primary chemical ideas can and may be utilized to man made difficulties. eventually, Kay Brummond introduces us to a brand new model of the Pauson-Khand reactions, person who will without doubt be additional exploited in effective methods by means of her staff good into the longer term.
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Additional resources for Advances in Cycloaddition, Volume 6 (Advances in Cycloaddition) (Advances in Cycloaddition)
Fleming, I. ; Pergamon: New York, 1991, Vol. 5, Chap. 1. 7. ; Wiley: New York, 1984. 52 JOSI 5 L. MASCAREI~IAS 8. For reviews and leading references, see: (a) Fisher, N. ; Olivier, E. ; Fisher, H. D. Fortschr. Chem. Org. Naturst. 1979, 38, 47. (b) Heathcock, C. ; Graham, S. ; Pirrung, M. ; Pavoac, E; White, C. T. ; Wiley: New York, 1983, Vol. 5, p. 333. (c) Rigby, J. H. ; Elsevier: Amsterdam, 1988, Vol. 12, p. 233. (d) Tanis, S. ; Robinson, E. ; McMiUs, M. ; Watt, W. J. Am. Chem. Soc. 1992, 114, 8349.
Ktbrich, G. Annalen 1961, 648, 114. 48. Mufioz, D. M. S. Dissertation, Universidad de Santiago, 1997. 49. (a) Mascarefias, J. ; Castedo, L. Synlett 1997, 81. (b) Ptrez, I. M. S. Dissertation, Universidad de Santiago, 1996. 50. ; Lautens, M. In Topics in Current Chemistry; Springer-Verlag: Berlin, 1997, Vol. 190, p. 1. 54 JOSl~ L. MASCAREI~IAS 51. (a) Williams, D. ; Benbow, J. ; McNutt, J. ; Allen, E. E. J. Org. Chem. 1995, 60, 833. (b) Molander, G. ; Eastwood, P. R. J. Org. Chem. 1995, 60, 8382.
1] architectures, most of these < OH DIBAL-H ( ~~ Scheme 42. RLi = < OH R The Chemistry of fl-Alkoxy-7- Pyrones 35 OH Y X or" Figure 10. methods require the presence of a C - C double bond in the furan unit of the oxabicycle in order to trigger the opening (Scheme 42), 5~although other tactics that rely on the generation of a radical or carbanion in the position o~ to the bridgehead carbon have also been used (Figure 10). 51'32 The presence of an electron-donating enol ether in the pyran portion of our [5+2] pyrone-alkene cycloadducts seemed to offer a particularly attractive site for launching the bridge opening, one that might be more effective after eliminating the conjugation with the ketone (Figure 11).
Advances in Cycloaddition, Volume 6 (Advances in Cycloaddition) (Advances in Cycloaddition) by Michael Harmata