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
, Jianzhang Zhao

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

42 Citations (SciVal)

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.

Original language	English
Pages (from-to)	1309-1315
Number of pages	7
Journal	Tetrahedron
Volume	64
Issue number	7
DOIs	https://doi.org/10.1016/j.tet.2007.11.061
Publication status	Published - 2008

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10.1016/j.tet.2007.11.061

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

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.",

author = "Xiaofen Liang and James, \{Tony D\} and Jianzhang Zhao",

year = "2008",

doi = "10.1016/j.tet.2007.11.061",

language = "English",

volume = "64",

pages = "1309--1315",

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T1 - 6,6′-Bis-substituted BINOL boronic acids as enantioselective and chemoselective fluorescent chemosensors for D-sorbitol

AU - Liang, Xiaofen

AU - James, Tony D

AU - Zhao, Jianzhang

PY - 2008

Y1 - 2008

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/37649019736

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

U2 - 10.1016/j.tet.2007.11.061

DO - 10.1016/j.tet.2007.11.061

M3 - Article

SN - 0040-4020

VL - 64

SP - 1309

EP - 1315

JO - Tetrahedron

JF - Tetrahedron

IS - 7

ER -

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

Abstract

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