Organotin-Mediated Synthesis of Macrocyclic Tetraesters: Regio- and Stereochemistry

Article abstract of DOI:10.1021/jo00272a036

The reaction of 4-phenyl- and 4-methyl-substituted dioxastannolanes (1 and 2, respectively) with glutaryl chloride has been investigated to provide a clear description of the regio- and stereochemistry of the organotin-mediated synthesis of macrocyclic tetraesters.In contrast with previous reports, the reaction does not exhibit the described regio- and stereospecificity, affording all possible isomers in substantial amounts, in line with the expected product distribution for a thermodynamically controlled reaction.The regioisomeric preference, that has been observedto some extent for the phenyl derivatives, appears to be unpredictably dependent on the substituent nature.Although experimental conditions can be optimized for reasonable yields of dimeric tetraester, the regio- and stereochemical outcome of this reaction cannot be readily predicted.