Direct Synthesis of Tetrasubstituted Dienoates by the Strain-Induced “Cut-and-Sew” Strategy of Carbon−Carbon Bonds

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The selective cleavage and functionalization of C−C bonds represent a powerful frontier in molecular editing and skeletal reconstruction. We report here a Lewis acid-catalyzed strategy for the formal insertion of propargyl alcohols into the C═C bond of benzoxazine-enaminones under ambient conditions. This “cut-and-sew” cascade enables the precise assembly of highly functionalized tetrasubstituted dienoates with excellent regioselectivity. The protocol is characterized by its broad substrate scope, high chemical yields, and the ability to reorganize unstrained carbon frameworks at room temperature, providing a versatile platform for the divergent synthesis of complex polyenes.