By Gordon W. Gribble and Thomas L. Gilchrist (Eds.)
This quantity of development in Heterocyclic Chemistry (PHC) is the fourteenth annual assessment of the literature, protecting the paintings released on very important heterocyclic ring structures in the course of 2001. during this quantity there are really expert studies. the 1st, by means of Jan Bergman and Tomasz Janosik, covers their paintings on sulfur-containing indoles. the second one, through David Knight, discusses five- endo -trig iodocyclisations. the following chapters, prepared through expanding heterocycle ring dimension, evaluation fresh advances within the box of heterocyclic chemistry with emphasis on synthesis and reactions.
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Extra info for A Critical Review of the 2001 Literature Preceded by Two Chapter on Current Heterocyclic Topics
For example, in an extension of the forcgoing methodology, iodocyclization of the hydroxy-amides 71 under standard conditions gives slowly but exclusively the annulated tetrahydrofurans 72 and not the corresponding spiro-oxetanes, as reported in a preliminary communication <97JOC5048>. This example also shows that it is possible to obtain a tertiary iodide from this chemistry, negating a conclusion from our initial studies. Simpler chiral oxazolidinone derivatives having a single distal substituent on the alkene group also give tetrahydrofurans 73 with some loss of stereoselection at the ncw m-carbon while cyclizations onto simple vinyl groups give only iodomethyloxetanes [cf.
I RO OH G3 Et20' _78oc R ,, R = TBDPS, Pri, Trt 54 A logical extension of this principle is to reduce it to its simplest form by replacing the activating furan with a vinyl ether function. The control inherent in this idea has been elegantly illustrated by Lipshutz and Tirado <94JOC8307> in the overall 5-endo cyclization of the polyfunctional substrate 55 which gives the five-membered cyclic acetal 56 almost exclusively. Similarly, a protected sugar derivative 57 can be generated in 75% isolated yield.
BnO'~l~"~ OH Et20, -78~ I..... ,~0 The same idea has been applied to the deconjugated aldol systems examined by Galatsis. Thus, exposure of the vinyl ether 58 to the 'standard' iodocyclization conditions gives the acetal 59, accompanied by the corresponding de-iodo derivative, which was presumably formed by acid-catalysed cyclizalion <95TL8179>. Stereoselection was higher at lower temperatures in acetonitrile. Presumably, the same mechanism is in operation in the useful bromine-induced cyclization of the [3-1actam 60 to give only the annulated derivative 61 <94TL6317>.
A Critical Review of the 2001 Literature Preceded by Two Chapter on Current Heterocyclic Topics by Gordon W. Gribble and Thomas L. Gilchrist (Eds.)