Grob-type fragmentation of an oxonium ylide generated from α-imino rhodium carbene

Abstract

A Grob-type fragmentation of an oxonium ylide generated from the intramolecular addition of oxygen to α-imino rhodium carbene was realized. The reaction was stereospecific and produced two remote double bonds. The newly formed double bonds could be employed as useful synthetic handles for further transformations. A reasonable mechanism was proposed based on primary control experiments and comparison of the stereochemistry of the starting triazoles with that of the products.