Affiliation:
1. Department of Chemistry University of Liverpool Crown Street Liverpool L69 7ZD UK
2. School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS UK
Abstract
AbstractTFA 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(sp3)‐rich polyheterocycles of relevance to medicinal chemistry.
Funder
College of Engineering, University of Canterbury
University of Liverpool