Rhodium Catalyzed Allene Amination: Diastereoselective Synthesis of Aminocyclopropanes via a 2-Amidoallylcation Intermediate

摘要

Our recent investigations into metallonitrene initiated cascade reaction processes lead us to postulate that an electrophilic metallonitrene could interact with an allene to generate an intermediate with a reactivity resembling that of a 2-amidoallylcation (Figure 1).rnHistorically, related trimethylenemethane and 2-oxyallylcation species have proven particularly useful for the construction of complex carbo- and heterocyclic molecules. New methods to generate and control these powerful synthons remain the focus of many contemporary research groups. Additionally allene epoxi-dation has been developed into a useful tool for complex molecule synthesis, and these studies provide insight into possible reaction pathways. However, despite the prevalence of nitrogen functionality in pharmaceutically important molecules, conceptually related 2-amidoallylcations have received considerably less attention.