Professor David Procter.
School of Chemistry
Tel.: 0161 275 1245
Related Web pages: people.man.ac.uk/~mbdssdp2
Rational design in organic synthesis. Solid-phase synthesis. The use of fluorous-tags in synthesis.
We have developed a new linker for the solid phase organic synthesis and have explored its utility for the synthesis of hetercyclic compounds. These studies led us to develop an improved strategy using a soluble fluorous tag in place of the insoluble polymer tag.
Our method is based on the addition of fluorous thiols to glyoxamides which act as a trigger that, when attacked by the thiol, captures the fluorous phase tag (RF) in a facile Pummerer cyclization thereby embedding the tag in the framework of the heterocycle. Thus in one step the fluoruos tag is introduced and the heterocyclic ring system is build. We call this process fluorous phase Pummerer cyclative capture
After cyclative capture, the fluoruos-tagged heterocyclic systems can be modified in a variety of ways and fluoruos solid phase extraction (FSPE) can be used for the rapid purification of intermediates. When the fluorous tag is no longer required, we can simply remove it.
A fluorous, Pummerer cyclative-capture strategy for the synthesis of N-heterocycles, L. A. McAllister, R. A. McCormick, K. M. James, S. Brand, N. Willetts, D. J. Procter, Chemistry - A European Journal, 2007, 13, 1032-1046.
A fluorous-phase Pummerer cyclative-capture strategy for the synthesis of nitrogen heterocycles, L. A. McAllister, R. A. McCormick, S. Brand, D. J. Procter, Angew. Chem., Int. Ed., 2005, 44, 452-455.