Abstract
The conventional Bergman pathway of enediynes to generate diradicals has to overcome a high reaction barrier, which limits the design of enediynes embedded inside a highly strained ring. Here, we proposed an alternative reaction mechanism. By converting the originally inactive enediyne into enyne-allene through possible 1,4-Michael addition, the low barrier Myers-Saito cyclization was triggered. Although direct addition of water or methanol was impossible due to high activation barrier, the 1,4-Michael addition was feasible with the assistance of intermolecular proton transfer at physiological temperature. This mechanism opens a new strategy in the design of structurally simple acyclic enediynes.
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