Formose reaction controlled by boronic acid compounds

• Toru Imai,
• Tomohiro Michitaka and
• Akihito Hashidzume

Beilstein J. Org. Chem. 2016, 12, 2668–2672, doi:10.3762/bjoc.12.263

• macromolecular boronic acid compounds, i.e., sodium phenylboronate (SPB) and a copolymer of sodium 4-vinylphenylboronate with sodium 4-styrenesulfonate (pVPB/NaSS), respectively. The boronic acid compounds provided different selectivities; sugars of a small carbon number were formed favorably in the presence of

• SPB, whereas sugar alcohols of a larger carbon number were formed preferably in the presence of pVPB/NaSS. Keywords: boronic acid compounds; formose reaction; sodium phenylboronate; sodium 4-vinylphenylboronate/sodium 4-styrenesulfonate copolymer; sugar alcohols; sugars; Findings When an aqueous

• optimizing the conditions of the formose reaction [6][7][8][9][10][11][12][13][14][15]. However, the selective formose reaction is still an important subject of investigation [16]. It is known that boronic acid compounds form esters with diols, e.g., sugars [17][18]. Boronic acid compounds may thus stabilize