One-Pot Synthesis of Nitrogen Heterocycles Initiated by Regio- and Diastereoselective Carbon-Carbon Bond Formation of Bifunctional Carbonyl Compounds

摘要

Tin-oxygen bonds can be easily generated by the addition of organotin nucleophiles to carbonyl compounds. Although the allylation of carbonyl compounds by allylic tins is a well-known method for carbon-carbon bond formation, the resulting tin alkoxides have been scarcely used for further transformation in which most tin-oxygen bonds are hydrolyzed to homoallylic alcohols. However, tin-oxygen and tin-nitrogen bonds bear high nucleophilicity. In some cases, their nucleophilicity is higher than that of the corresponding free alcohols and amines. Herein, we report a one-pot synthesis of nitrogen heterocyclic compounds initiated by the allylation of the formyl group of bifunctional carbonyl compounds 1. The generated tin-oxygen bonds worked as key intermediates to prepare various heterocyclic compounds accompanying chemo-, regio-, and diastereoselective carbon-carbon bond formation in the side chain moieties (Scheme 1).