1018389-92-8Relevant articles and documents
A fluorous-tagged linker from which small molecules are released by ring-closing metathesis
Leach, Stuart G.,Cordier, Christopher J.,Morton, Daniel,McKiernan, Gordon J.,Warriner, Stuart,Nelson, Adam
, p. 2753 - 2759 (2008/09/19)
(Chemical Equation Presented) A fluorous-tagged linker for the parallel synthesis of small- and medium-ring and macrocyclic nitrogen heterocycles using ring-closing metathesis is described. The linker was designed such that "cyclization-release" of the cyclic heterocyclic products was coupled with liberation of the active catalyst. The design of the linker was validated using a non-fluorous-tagged model. A wide range of unsaturated alcohols were used as reagents to functionalize afluorous-tagged sulfonamide, (Z)-{N-[4-(2-(N′-3,3,4,4,5,5,6,6,7,7,8,8,9,9,-10,10,10- heptadecafluorodecyl)-4-methylsulfonamido)methylallyloxy]but-2-enyl} -2-nitrobenzene-sulfonamide, using Fukuyama-Mitsunobu reactions; in each case, fluorous-solid-phase extraction (F-SPE) was used to purify the functionalized linker from the excess reagents. In general, the "cyclization-release" of cyclic products was triggered using a light-fluorous tagged derivative of the Grubbs-Hoveyda second-generation catalyst. After the metathesis step, F-SPE was used to purify released cyclic compounds from the fluorous-tagged linker and the fluorous-tagged catalyst. The scope and limitations of the approach were determined using a range of substrates which probed different aspects of the functionalization and metathesis steps. In the study as a whole, a wide range of small- and medium-ring and macrocyclic nitrogen heterocycles were prepared using polyene and polyenyne metathesis cascades.
