Synthesis of Simple 3,3-Diarylazetidines from <i>N</i>-Boc-3-arylazetidinols Using Friedel–Crafts Arylation Conditions
Madhurima Das, Amber Weissenfluh, Nam Tung Ly, Mark L. Trudell
Abstract
A synthesis of 3,3-diarylazetidines from N-Boc-3-aryl-3-azetidinols using Friedel–Crafts arylation conditions with AlCl3 is described. A series of substituted diarylazetidines were readily prepared and isolated as the oxalate salts in high yield and high purity. The 3,3-diarylazetidine oxalates were then easily converted into N-alkyl and N-acyl analogues (RX, NaHCO3/DMF/100 °C) in high overall yields.
Topics & Concepts
ChemistryFriedel–Crafts reactionYield (engineering)ArylOxalateAlkylOrganic chemistrySimple (philosophy)CatalysisEpistemologyPhilosophyMetallurgyMaterials scienceSynthesis of β-Lactam CompoundsSynthesis and Catalytic ReactionsAsymmetric Synthesis and Catalysis