Acyclic, selective esterification

At this point of the synthesis the Fe(CO)3 fragment has done its job and is oxidatively removed. Hydrolysis, decarboxylation and re-esterification then afford the desired intermediate 5. With the aid of the small iron fragment, the synthesis of the acyclic intermediate 5 has been achieved in a short, highly selective sequence. Thus, the problem of the stereocontrolled generation of distant stereocenters (1,6 asymmetric induction) was solved in an elegant manner. 

A detailed study on the conventional benzoylation and pivaloylation of d-fructose has been undertaken following consideration of factors such as equilibration rates and the distribution of tautomeric forms at given temperatures, practical procedures for the selective preparation of either pyranose, furanose, or acyclic peresters have been worked out. The selectivities in electrochemically induced esterifications of D-glycals have been investigated and compared with selectivities in chemically induced ester formations. ... 

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