Linkers and Cleavage Strategies in Solid-Phase Organic Synthesis and Combinatorial Chemistry

Fabrice Guillier; David Orain; Mark Bradley
Chem. Rev., 2000, 100, 2091−2157
https://doi.org/10.1021/cr980040+

Abstract

The massive increase in the number of papers describing the use of polymeric supports in organic synthesis over the past decade is a vivid demonstration of its impact in the chemical community. Few other changes in synthetic chemistry methodology have displayed such a growing passion or had such a profound influence on the way synthetic chemistry is carried out. The advantages gained by this methodology are striking, with four main factors contributing to the popularity of the technique. (i) The ease of chemistry. Reactions can be accomplished in only three steps:  addition of reagents, filtering, and washing the resin, thus allowing many simple automated procedures to be developed. (ii) The elimination of purification steps en route. For each step of a multiple-step synthesis, the only purification needed is a resin-washing step. Only the final product of cleavage needs to be purified. (iii) In a solid-phase synthesis, high concentrations of reagents can be used to drive reactions to completion. (iv) The straightforward nature of parallel solid-phase synthesis.

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