Bridgehead bicyclic unsaturated enamines were prepared by a tandem rhodium-catalyzed C−H bond activation/alkenylation/electrocyclization of alkyne-tethered unsaturated imines. These strained bicyclic enamines exhibit unique reactivity: for example, they give N -alkylated products upon treatment with alkylating reagents and undergo double-bond isomerization to alleviate ring strain upon reduction.
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Yotphan et al. (2008) studied this question.
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