A Stereospecific Alkene 1,2‐Aminofunctionalization Platform for the Assembly of Complex Nitrogen‐Containing Ring Systems
Yuxiang Zhu, Matthew J. S. Smith, Wenbin Tu, John F. Bower
Abstract
Abstract TFA promoted deprotection of O−Ts activated N‐Boc hydroxylamines triggers aminofunctionalization‐based polycyclizations of tethered alkenes. The processes involve intramolecular stereospecific aza‐Prilezhaev alkene aziridination in advance of stereospecific C−N cleavage by a pendant nucleophile. Using this approach, a wide range of fully intramolecular alkene anti ‐1,2‐difunctionalizations can be achieved, including diaminations, amino‐oxygenations and amino‐arylations. Trends associated with the regioselectivity of the C−N cleavage step are outlined. The method provides a broad and predictable platform for accessing diverse C(sp 3 )‐rich polyheterocycles of relevance to medicinal chemistry.