By Gordon W. Gribble and Thomas L. Gilchrist (Eds.)
This quantity of growth in Heterocyclic Chemistry (PHC) is the fourteenth annual overview of the literature, masking the paintings released on vital heterocyclic ring structures in the course of 2001. during this quantity there are really expert studies. the 1st, through Jan Bergman and Tomasz Janosik, covers their paintings on sulfur-containing indoles. the second one, by means of David Knight, discusses five- endo -trig iodocyclisations. the next chapters, prepared by means of expanding heterocycle ring dimension, assessment contemporary advances within the box of heterocyclic chemistry with emphasis on synthesis and reactions.
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Extra resources for A Critical Review of the 2001 Literature Preceded by Two Chapter on Current Heterocyclic Topics
We were unamused to find that the only product obtained 46 was indeed that arising from 5-exo cyclization, with complete loss of the 'protecting' group, hence spelling the end of this particular target synthesis! / Me 45 CO2Me ~. ~ C O 2 M e I OH 46 Another caution regarding protecting groups concerns the masking of carboxylic acid functions. Methyl esters are probably the best blocking groups, but even these can be lost, as such esters can participate in 5-exo iodocyclizations (see 18 above). It is therefore perhaps stating the obvious that both t-butyl and benzyl esters are less stable under such reaction conditions.
In any event, the conformation 93 provides a basis for synthetic design, if nothing else, and can also in principle be used to account for the outcomes of cyclizations of more highly substitutcd precursors. Z ,I- ".. | E ~0"' MeO H ' / 93 ~ ~ Z ";, E ~ I " ,,E OH Z Z 'syn' 94 95 96 | OH Z 97 ~, I ...... Z ~nfi' 98 99 100 However, some doubt as to the validity of this conclusion arose from the work of Lipshutz and Barton <92JA1084> who suggested, for example, that iodocyclization of the anti-(E)- homoallylic alcohol [98; Z = H] led to an all-cis-iodotctrahydrofuran.
Me 45 CO2Me ~. ~ C O 2 M e I OH 46 Another caution regarding protecting groups concerns the masking of carboxylic acid functions. Methyl esters are probably the best blocking groups, but even these can be lost, as such esters can participate in 5-exo iodocyclizations (see 18 above). It is therefore perhaps stating the obvious that both t-butyl and benzyl esters are less stable under such reaction conditions. Certainly our experience with esters 47 was that poorer yields of the iodotetrahydrofurans 48 were obtained due to loss of the ester groups during competing 6-exo cyclization.
A Critical Review of the 2001 Literature Preceded by Two Chapter on Current Heterocyclic Topics by Gordon W. Gribble and Thomas L. Gilchrist (Eds.)