Exploring a benzyloxyaniline linker utilizing ceric ammonium nitrate (CAN) as a cleavage reagent: solid-phase synthesis of N-unsubstituted beta-lactams and secondary amides.
[figure: see text] A novel benzyloxyaniline linker that uses ceric ammonium nitrate (CAN) as a cleavage reagent is described. Its application in the solid-phase synthesis of N-unsubstituted beta-lactams and secondary amides furnishes compounds in moderate to excellent yield (45-91%) and high purity (93-99%).
Gordon
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KH
University Chemical Laboratory, University of Cambridge, Cambridge CB2 1EW, U.K.
Balasubramanian
S
S
D000577:Amides / Q000138:chemical synthesis*; D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D002563:Cerium / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017550:Spectroscopy, Fourier Transform Infrared; D013329:Structure-Activity Relationship; D013431:Sulfates / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry; D047090:beta-Lactams / Q000138:chemical synthesis*
D000577:Amides; D000814:Aniline Compounds; D013431:Sulfates; D014753:Vinyl Compounds; D047090:beta-Lactams; C100195:vinyl ether; D002563:Cerium; C082771:ceric ammonium sulfate