Twists and turns of lactam research

Abstract

The importance of the amide bond cannot be overstated. Typical amides are planar structures, however, amide bonds can be highly twisted such as in bicyclic bridgehead lactams. The distortion of the orbitals from planarity and the pyramidalization of the nitrogen from sp toward sp dramatically affect the stability and reactivity of anti-Bredt amides. In 2006, our group published the first unambiguous synthesis and characterization of 2- quinuclidonium tetrafluoroborate. Since then we have been fascinated with the synthesis and characterization of such strained reactive lactams. We have also pursued the synthesis of a series of novel stereogenic lactams that can be employed as intermediates in multi-step synthesis. The lecture will discuss our efforts in these vibrant research areas. Looking ahead, the limits are still open for the synthesis of more or less reactive but structurally unique and often twisted amides.