By Gordon W. Gribble and Thomas L. Gilchrist (Eds.)
This quantity of growth in Heterocyclic Chemistry (PHC) is the fourteenth annual evaluation of the literature, masking the paintings released on vital heterocyclic ring platforms in the course of 2001. during this quantity there are really good reports. the 1st, through Jan Bergman and Tomasz Janosik, covers their paintings on sulfur-containing indoles. the second one, by way of David Knight, discusses five- endo -trig iodocyclisations. the next chapters, prepared through expanding heterocycle ring dimension, overview 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
W. Knight 38 A conceptually different approach to the asymmetric synthesis of tetrahydrofurans by selenocyclization is to employ a chiral, non-racemic selenium reagent. Although the majority of studies have focussed on 5-exo cyclizations, a few feature 5-endo modes and are restricted to homoallylic alcohols which do not already contain an asymmetric centre, as the latter should of course be capable of providing control without the requirement for a relatively sophisticated chiral selenium-based reagent.
R2 163 ,,SeAr* R1, R2 = H, Me 165 In contrast to the success of 5-endo-trig cyclizations using selenium-based electrophiles, related reactions with sulfenyl reagents are, as yet, not as successful. Intramolecular sulfenyl etherification in general using N-(phenylthio)morpholine requires an acid promoter such as triflic acid but works poorly with 3-butenol, unless TMSOTf is used when the phenylsulfenyl tetrahydrofuran 166 is formed in 47% yield <87CC1280>. In contrast, phenyl- or methylsulfenyl chlorides produce only the alkene addition product 167 <87TL523>.
1 ~ OMe H 82 tL! ~ OMe H 83 84 I ; H C02Me 85 As much to prove the nature and stereochemistry of the products 80 as to demonstrate a use of this chemistry, we have applied it to a brief synthesis of D-(-)-muscarine 89, the enantiomer of a powerful acetylcholine agonist present in the fly agaric mushroom, Amanita muscara <94SL295>. Starting with dimethyl (S)-malate on cost grounds, known chemistry <90T4277; 83TL391; 01TL6947> provided the (Z)-unsaturated hydroxy-ester 86. Exposure of this to IJ]XlaHCO3 gave the expected hydroxytetrahydrofuran 87 in 84% yield.
A Critical Review of the 2001 Literature Preceded by Two Chapter on Current Heterocyclic Topics by Gordon W. Gribble and Thomas L. Gilchrist (Eds.)