One-carbon extension

Silyl enol ether (38), derived from D-glucose, undergoes a useful one-carbon extension by way of an asymmetric aldol reaction the conditions of the indium(ni) catalysis in water are very convenient. 

Thiazole-Based One-Carbon Extension of Carbohydrate Derivatives... 

Scheme 26 Method for the free radical-mediated one carbon extension of unactivated alkenes...

Scheme 27 Application of the one carbon extension approach to carbohydrates...

Homologation is the one-carbon extension reaction of organic compounds such as alcohols and carboxylic esters, and is very important. Cobalt, rhodium, and ruthenium complexes are known to be efficient catalysts. Methanol and methyl ester can be converted to ethanol and ethyl ester, respectively, using Ru/F [28] and Ru/Co [29] catalysts (Eq. 11.9). 

Dondoni, A, Marra, A, Thiazole-based one-carbon extension of carbohydrate derivatives. In Preparative Carbohydrate Chemistry, Hanessian, S, ed., Marcel Dekker, New York, pp. 173-205, 1997. 

Thiazole-based one carbon extension has been proved to be a useful tool in the synthesis of C-branched sugar derivatives [37]. To investigate an approach towards the synthesis of... 

Direct cyanations to sugars or sugar derivatives, represented in Figure 2.2.1, effect one carbon extensions. The resulting nitriles are then available for a number of further reactions including cycloadditions, hydrolyses to acids, and reduction to aminomethyl groups. Unfortunately, there are no stereospecific methods available for these reactions. 

---