The development of a novel Dipolar Alkynyl-Prins (DAP) protocol for the expedient synthesis of unique, sp<sup>3</sup>-rich complex polycycles is described. This method relies upon a coupling of amphielectronic alkynyl and acetal building blocks under acidic conditions. The one-pot transformation consists of an intramolecular Prins cyclization of an alkyne and oxocarbenium ion (generated from an alcohol-acetal condensation), followed by nucleophilic capture of the incipient vinyl cation by the pendant (protected) amine functionality to furnish oxa-aza fused bicycles in a highly general, efficient and stereocontrolled fashion. In this reaction cascade, molecular complexity is rapidly generated as three new bonds (C-C, C-O, and C-N) as well as two new rings are formed in one synthetic operation from simple and convenient precursors.

Dipolar alkynyl-prins (DAP) cyclization for the rapid construction of complex polycycles

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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