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

Xiaofen Liang, Tony D James, Jianzhang Zhao

Research output: Contribution to journalArticle

37 Citations (Scopus)

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 languageEnglish
Pages (from-to)1309-1315
Number of pages7
JournalTetrahedron
Volume64
Issue number7
DOIs
Publication statusPublished - 2008

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