Regio- and Stereoselective Addition of Brønsted Acids to Yndiamides: Synthesis of N,O,N- and N,S,N-Trisubstituted Ketene Acetals

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AbstractYndiamides, N,N-disubstituted alkynes, are versatile building blocks for the synthesis of nitrogen-containing organic molecules. Unlike ynamides, relatives that are inherently polarized by a single nitrogen substituent, their pseudo-symmetric nature renders regioselective reactions challenging. Here we report investigations into the regio­selective addition of Brønsted acids to non-symmetric yndiamides, a reaction that delivers N,O,N- and N,S,N-trisubstituted ketene acetals with excellent regio- and stereoselectivity.