Catalytic Formation of Monosaccharides: From the Formose Reaction towards Selective Synthesis

• Published in: ChemSusChem 2014-07, Vol.7 (7), p.1833-1846
• Main Authors: Delidovich, Irina V., Simonov, Alexandr N., Taran, Oxana P., Parmon, Valentin N.
• Format: Article
• Language: English
• Subjects: aldol reaction; autocatalysis; biomass; carbohydrates; Carbohydrates - chemistry; Catalysis; Chemistry Techniques, Synthetic - methods; Formaldehyde - chemistry; homogeneous catalysis; Kinetics; Monosaccharides - chemical synthesis
• ISSN: 1864-5631; 1864-564X
• DOI: 10.1002/cssc.201400040

The formose reaction (FR) has been long the focus of intensive investigations as a simple method for synthesis of complex biologically important monosaccharides and other sugar‐like molecules from the simplest organic substrate—formaldehyde. The fundamental importance of the FR is predominantly connected with the ascertainment of plausible scenarios of chemical evolution which could have occurred on the prebiotic Earth to produce the very first molecules of carbohydrates, amino‐ and nucleic acids, as well as other vitally important substances. The practical importance of studies on the FR is the elaboration of catalytic methods for the synthesis of rare and non‐natural monosaccharides and polyols. This Minireview considers the FR from the point of view of chemists working in the field of catalysis with emphasis on the mechanisms of numerous parallel and consequent catalytic transformations that take place during the FR. Based on its kinetics, the FR may be considered as a non‐radical chain process with degenerate branching. The Minireview also considers different approaches to the control of selectivity of carbohydrate synthesis from formaldehyde and lower monosaccharides. First and formose: The formose reaction (FR) is a simple method for synthesis of complex sugar‐like molecules from the simplest organic substrate—formaldehyde. This Minireview outlines the mechanisms of numerous parallel and consequential chemical transformations that take place during the FR. The different approaches to the control of selectivity of carbohydrate synthesis from formaldehyde and lower monosaccharides are also considered.