The stepwise cycloaddition/cycloreversion Chauvin mechanism typically entails the participation of a transition metal alkylidene complex as the catalyst. Olefincarbonyl metathesis has recently emerged as an alternative mechanistic framework for expanding synthetic design into the heteroatom regime. The reaction development witnesses the evolution from an initial Paternò-Büchi type oxetane synthesis-fragmentation approach, to a subsequent metal alkylidenemediated scheme, and eventually to a Lewis acid-or organocatalysis strategy. In this synthetic scenario, the metal alkylidene complex is not catalytically competent due to the intrinsically limited electronic tunability of C=O π bond and low reactivity of the intermediately formed [M]=O bond; the Lewis acid-and organocatalysis frequently rely on thermodynamically favored ring strain release (reactant) or ring structure formation (product) as a driving force completing a reaction. In contrast to the olefin-carbonyl metathesis, olefin-imine metathesis remains a virtually untapped area and only one stoichiometric metal alkylidene-mediated process has been documented lately (Scheme 1A). The broad electronic tunability of C=N π bond (hydrazone, oxime) allows the energy/polarity-enabled matching of its reactivity with that of the metal alkylidene complex; however, a similar trap presumably in the low-reactivity [M]=NR bonding species renders the catalytic turnover inaccessible. We have proposed and demonstrated the use of enaminone as a synthon for C-H bond functionalization reactions. These synthetic endeavors have led to the discovery of new reactivity patterns for this electronically push-pull structural motif. In an effort to further expand the reactivity profile of enaminone, the C β =C α bond is targeted as a potentially viable reactive site. The reaction partner is selected to be amidine due to the presence of imine group in a distinct structural context (linked to an amine group) as compared with a typical, isolated imine group; the imine group can undergo the nucleophilic exchange reaction with the -NR 2 portion of enaminone and consequently, the C=N bond can likely be engaged in an intramolecular reaction with the C β =C α portion of enaminone