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A Stereospecific Alkene 1,2-Aminofunctionalization Platform for the Assembly of Complex Nitrogen-Containing Ring Systems.

Yuxiang ZhuMatthew J S SmithWenbin TuJohn F Bower
Published in: Angewandte Chemie (International ed. in English) (2023)
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.
Keyphrases
  • high throughput
  • dna binding
  • energy transfer
  • transcription factor
  • single cell