Diastereoselective Self-Condensation of Dihydroxyfumaric Acid In Water: Potential Route to Sugars

摘要

Dihydroxyfumaric acid (DHF, 1, Scheme 1) has a long history since the days of its synthesis and extensive studies by Fenton in the 1890s. The chemistry of DHF and that of itscorresponding ester derivatives in organic solvents has been investigated. However, studies of the (non-enzymatic) aqueous chemistry of DHF have been sparse, perhaps as result of a) its perceived "instability" in aqueous solutions owing to its oxidative transformation into dioxosuccinic acid and its more widely known decarboxylative conversion into glycolaldehyde (Scheme 1), and b) the sparing solubility not only of the parent acid, but also of its Na~+, K~+, and NH4~+ salts, in water.