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Additional resources for Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials (Volume 1 and 2), Second Edition

Sample text

2) were demonstrated to complex glycopyranosides weakly [151] and these units have been employed in the design of “synthetic lectins” (Chapter 13). Fluorescent catechol derivatives such as the dye alizarin red S (ARS) also form covalent adducts with boronic acids in water, and this equilibrium has been used as a competitive color- and fluorescence-based assay for both qualitative and quantitative determination of saccharide binding [152]. Using the ingenious ARS assay, Springsteen and Wang presented an interesting cautionary tale from discrepancies found in the measurements of boronic acid–diol binding constants based on the above-mentioned method of pH depression [141].

More important factors affecting the equilibrium are the effect of steric repulsions on enthalpy and the entropies of internal rotation of the free diols. For example, trans-4,5-disubstituted dioxaborolanes such as DICHED esters present a minimal extent of steric repulsions as the two cyclohexyl substituents eclipse CÀH bonds. On the contrary, pinacol esters present a significant amount of steric repulsion from the four eclipsing methyl groups. Consequently, it is not surprising that pinacol esters can be transesterified easily with trans-DICHED so as to relieve these eclipsing interactions [15, 136].

Two-phase transesterification procedures with polystyrylboronic acid [130] or with phenylboronic acid have been described, but the latter is only applicable to small, water-soluble boronic acids [131]. Most of these procedures, such as the BCl3-promoted method, were applied to the particular case of pinanediol esters of a-acylaminoalkylboronic acids [22, 125]. 12) [132]. 9) can be effected under oxidative conditions, providing an orthogonal strategy to protect boronic acid compounds in various transformations [133].

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