Polymer-supported protective groups 1,3-diols

While our reaction was a solid-liquid-solid reaction, Hcylge s involved the use of concentrated aqueous sodium hydroxide and tetrabutyl ammonium hydroxide. It is noteworthy that the final polymer (IV) is much more effective in its use as a polymer-supported protecting group for carbonyl compounds (Ref. 29) than a somewhat similar polymer-bound diol prepared under standard conditions (Ref. 30, 31). 

One widely used method of formation of protected compounds involves polymer-supported reagents,21-27 with the advantage of simple workup by filtration and automated syntheses, especially of polypeptides. Polymer-supported reagents are used to protect a terminal —COOH group as a polymer-bound ester (RCOOR — ) during peptide syntheses,21 to protect primary alcohols as — trityl ethers,28 and to protect 1,2- and 1,3-diols as —phenyl boronates.29 Monoprotection of symmetrical dialdehydes and diacid chlorides has been reported 23 some diprotection occurs with diols and diamines.23... 

The concept of immobilizing diol compounds with a boronic acid conjugated support as a sort of heterogeneous protecting group strategy is the antipode of the diol-based supports described in Section 1.4.2. Examples of such boronic acid matrices include polystyryl boronic acid resins (120) [500-502], the cellulose-derived support 121 [503], the methacrylic polymer 122 [504], and the polyacrylamide-supported nitroarylben-... 

Hodl983 Hodge, P. and Waterhouse, J., Preparation of a Polymer-Supported Diol and Its Use in Isolating Aldehydes and Ketones from Mixtures and as a Protecting Group for Aldehydes and Ketones, J. Chem. Soc., Perkin Trans. 1, (1983) 2319-2323. 

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