6,6′-Bis-substituted BINOL boronic acids as enantioselective and chemoselective fluorescent chemosensors for D-sorbitol

Reference:

Liang, X., James, T. D. and Zhao, J., 2008. 6,6′-Bis-substituted BINOL boronic acids as enantioselective and chemoselective fluorescent chemosensors for D-sorbitol. Tetrahedron, 64 (7), pp. 1309-1315.

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Official URL:

http://dx.doi.org/10.1016/j.tet.2007.11.061

Abstract

A new chiral fluorescent BINOL boronic acid 1 has been synthesized. The chiral recognition properties of 1 are drastically different from BINOL boronic acid c. Sensor 1 shows improved enantioselectivity as well as chemoselectivity toward sugar alcohols, such as D-sorbitol and D-mannitol. The enantioselectivity of sensor 1 toward D-sorbitol (K-R/K-S) is 1:35 (pH 9.0), and the chemoselectivity for D-sorbitol/D-mannitol is 20:1.

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