1,2-Silyl Shift in Propargyl Silanes as a Novel Methodology for the Synthesis of Heterocycles and Substituted Olefins

The Doctoral Thesis is dedicated to the use of propargyl silanes for the synthesis of small-molecule heterocycles containing a stereochemically defined, highly functionalized double bond in the side chain. This is achieved by activating propargyl silanes with electrophiles to induce the 1,2-silyl shift, thus generating an allyl cation intermediate or its equivalent. Ring closure is achieved by subsequent attack by internal O-, N-, S-, or C-centred nucleophiles. In addition, the application of propargyl silanes under Ritter-type reaction conditions is investigated to afford products containing stereochemically defined allylamine fragments.