Utilization of N-Silyl Enamines from Borane-Catalyzed Hydrosilylation of Conjugated Nitriles for Formamidine and Ester Synthesis

초록

In recent research, we have developed a synthetic strategy to furnish Z-amidines from cyclic N-silyl enamines and organic azides via [3+2] cycloaddition following the rearrangement pathway. In this study, we have chosen the optimal conditions to obtain linear N-silyl enamines from borane-catalyzed hydrosilylation of conjugated nitriles. These linear N-silyl enamines also underwent [3+2] cycloaddition with organic azides, but triazoline intermediate occurred a different rearrangement pathway. With different features, we have developed a synthetic route to produce E-formamidines and utilized the co-products, being diazo alkanes, to produce ester with simple and mild condition.