By Michael Harmata
This quantity offers paintings from six various teams engaged on quite a few points of cycloaddition chemistry. Jos? Mascare?as provides us a really fascinating account of the chemistry of &Bgr;-alkoxy-&ggr;-pyrones and similar species. Al Padwa and Chris Staub talk about extra advances in rhodium carbenoid chemistry and the bizarre cycloaddition methods attainable with those intermediates. better order cycloadditions mediated by means of transition metals spotlight Jim Rigby's replace on his group's efforts during this zone. Lily Lee and John Snyder current us with an in depth account of the indole ring as a dienophile, demanding us to contemplate 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 kids who have to see how basic chemical rules can and will be utilized to artificial difficulties. eventually, Kay Brummond introduces us to a brand new model of the Pauson-Khand reactions, one who will without doubt be extra exploited in efficient methods through 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)
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. 52. Mascarefias, J. ; Castedo, L. J. Org. Chem. 1997, 62, 8620. 53. Rodffguez, J. ; Mascarefias, J. L. Presented at the 10th IUPAC OMCOS Symposium, Versailles (France), July 1999.
The cycloaddition does not work in protic solvents such as MeOH, with the rapid decomposition of the starting pyrone observed when the temperature was increased above 100 ~ Hence, toluene seems to be among the best solvents to carry out the reaction. 15 M. 36 As expected, the cycloaddition can also be accomplished using acyl esters as transferable groups, although this required heating at higher temperatures than with the corresponding silyl derivatives (Scheme 25). Among the acyl groups tested we found that the reaction of the p-nitrobenzoate (R = pNO2Bz, Scheme 25) is slightly faster than that of the benzoate (R = Bz), and this is, in turn, faster than that of the acetate (R = Ac) (approx.
67 The most recent report by Kozikowski shows that moderate levels of facial diastereoselectivity can be achieved in the cycloaddition of oxidopyridinium ylide 135 with (R)-p-tolyl vinyl sulfoxide (Scheme 55). 67b We briefly investigated an alternative approach to achieve diastereoselectivity in oxidopyridinium-alkene cycloadditions based on the introduction of the chiral auxiliary in the pyridinium dipole instead of the dipolarophile, by taking advantage of the relative ease of preparing pyridones from pyrones.
Advances in Cycloaddition, Volume 6 (Advances in Cycloaddition) (Advances in Cycloaddition) by Michael Harmata