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

Xiaofen Liang,Tony D James,Jianzhang Zhao

doi:10.1016/j.tet.2007.11.061

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

Xiaofen Liang, Tony D James + Show 1 more

https://doi.org/10.1016/j.tet.2007.11.061

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Journal: Tetrahedron	Publication Date: Nov 22, 2007
Citations: 40

Affiliation: Dalian University, Dalian University of Technology, University of Bath

#Sugar Alcohols #Chiral BINOL + Show 7 more

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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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